{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T22:49:33Z","timestamp":1788389373620,"version":"build-2803163510"},"reference-count":141,"publisher":"American Chemical Society (ACS)","issue":"13","license":[{"start":{"date-parts":[[2020,3,20]],"date-time":"2020-03-20T00:00:00Z","timestamp":1584662400000},"content-version":"vor","delay-in-days":14,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccby_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100004189","name":"Max-Planck-Gesellschaft","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100004189","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,4,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The marine macrolide chagosensine is supposedly distinguished by a (Z,Z)-configured 1,3-chlorodiene contained within a highly strained 16-membered lactone ring, which also incorporates two trans-2,5-disubstituted tetrahydrofuran (THF) rings; this array is unique. After our initial synthesis campaign had shown that the originally proposed structure is incorrect, the published data set was critically revisited to identify potential mis-assignments. The \u201cnorthern\u201d THF ring and the anti-configured diol in the \u201csouthern\u201d sector both seemed to be sites of concern, thus making it plausible that a panel of eight diastereomeric chagosensine-like compounds would allow the puzzle to be solved. To meet the challenge, the preparation of the required building blocks was optimized, and a convergent strategy for their assembly was developed. A key role was played by the cobalt-catalyzed oxidative cyclization of alken-5-ol derivatives (\u201cMukaiyama cyclization\u201d), which is shown to be exquisitely chemoselective for terminal alkenes, leaving even terminal alkynes (and other sites of unsaturation) untouched. Likewise, a palladium-catalyzed alkyne alkoxycarbonylation reaction with formation of an \u03b1-methylene-\u03b3-lactone proved instrumental, which had not found application in natural product synthesis before. Further enabling steps were a nickel-catalyzed \u201cTamaru-type\u201d homocrotylation, stereodivergent aldehyde homologations, radical hydroindation, and palladium-catalyzed alkyne-1,2-bis-stannation. The different building blocks were assembled in a serial fashion to give the idiosyncratic chlorodienes by an unprecedented site-selective Stille coupling followed by copper-mediated tin\/chlorine exchange. The macrolactones were closed under forcing Yamaguchi conditions, and the resulting products were elaborated into the targeted compound library. Yet, only one of the eight diastereomers turned out to be stable in the solvent mixture that had been used to analyze the natural product; all other isomers were prone to ring opening and\/or ring expansion. In addition to this stability issue, our self-consistent data set suggests that chagosensine has almost certainly little to do with the structure originally proposed by the isolation team.<\/jats:p>","DOI":"10.1021\/jacs.0c01700","type":"journal-article","created":{"date-parts":[[2020,3,6]],"date-time":"2020-03-06T12:28:21Z","timestamp":1583497701000},"page":"6409-6422","source":"Crossref","is-referenced-by-count":47,"title":["Chagosensine:\nA Riddle Wrapped in a Mystery Inside\nan Enigma"],"prefix":"10.1021","volume":"142","author":[{"given":"Marc","family":"Heinrich","sequence":"first","affiliation":[{"name":"Max-Planck-Institut fu\u0308r Kohlenforschung , ,","place":["Mu\u0308lheim\/Ruhr, Germany, D-45470"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John J.","family":"Murphy","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut fu\u0308r Kohlenforschung , ,","place":["Mu\u0308lheim\/Ruhr, Germany, D-45470"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marina K.","family":"Ilg","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut fu\u0308r Kohlenforschung , ,","place":["Mu\u0308lheim\/Ruhr, Germany, D-45470"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aure\u0301lien","family":"Letort","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut fu\u0308r Kohlenforschung , ,","place":["Mu\u0308lheim\/Ruhr, Germany, D-45470"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jakub T.","family":"Flasz","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut fu\u0308r Kohlenforschung , ,","place":["Mu\u0308lheim\/Ruhr, Germany, D-45470"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Petra","family":"Philipps","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut fu\u0308r Kohlenforschung , ,","place":["Mu\u0308lheim\/Ruhr, Germany, D-45470"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0098-3417","authenticated-orcid":true,"given":"Alois","family":"Fu\u0308rstner","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut fu\u0308r Kohlenforschung , ,","place":["Mu\u0308lheim\/Ruhr, Germany, D-45470"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,3,6]]},"reference":[{"key":"2026090114525402900_cit1","doi-asserted-by":"publisher","first-page":"13575","DOI":"10.1002\/anie.201808937","article-title":"Total Synthesis of Putative Chagosensine","volume":"57","author":"Heinrich","year":"2018","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit2","doi-asserted-by":"publisher","first-page":"4073","DOI":"10.1002\/ejoc.200300240","article-title":"Chagosensine, a New Chlorinated Macrolide\nfrom the Red Sea Sponge Leucetta chagosensis","volume":"2003","author":"R\u030cezanka","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"2026090114525402900_cit3a","doi-asserted-by":"publisher","first-page":"6372","DOI":"10.1021\/jacs.6b02653","article-title":"Tandem\nOlefin Metathesis\/Oxidative Cyclization: Synthesis of Tetrahydrofuran\nDiols from Simple Olefins","volume":"138","author":"Dornan","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit3b","doi-asserted-by":"publisher","first-page":"e1900131","DOI":"10.1002\/hlca.201900131","article-title":"Multi-Gram Scale Synthesis\nof Chiral 3-Methyl-2,5-trans-tetrahydrofurans","volume":"102","author":"Qin","year":"2019","journal-title":"Helv. Chim. Acta"},{"key":"2026090114525402900_cit3c","doi-asserted-by":"publisher","first-page":"49541","DOI":"10.1039\/C5RA06640A","article-title":"Efficient access to polysubstituted tetrahydrofurans\nby electrophilic cyclization of vinylsilyl alcohols","volume":"5","author":"Barbero","year":"2015","journal-title":"RSC Adv."},{"key":"2026090114525402900_cit3d","doi-asserted-by":"publisher","first-page":"11994","DOI":"10.1002\/chem.201501655","article-title":"A New Strategy for Enantioselective Construction of\nMultisubstituted Five-Membered Oxygen Heterocycles via a Domino Michael\/Hemiketalization\nReaction","volume":"21","author":"Hua","year":"2015","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit3e","doi-asserted-by":"publisher","first-page":"1542","DOI":"10.1021\/acs.orglett.6b00303","article-title":"Stereocontrolled (Me3Si)3SiH-Mediated\nRadical and Ionic Hydride Transfer in Synthesis of 2,3,5-Trisubstituted\nTHF","volume":"18","author":"Gre\u0301laud","year":"2016","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit4a","doi-asserted-by":"publisher","first-page":"4044","DOI":"10.3390\/md13074044","article-title":"Biological\nActivity of Recently Discovered Halogenated Marine Natural Products","volume":"13","author":"Gribble","year":"2015","journal-title":"Mar. Drugs"},{"key":"2026090114525402900_cit4b","doi-asserted-by":"publisher","first-page":"4396","DOI":"10.1002\/anie.201506388","article-title":"Stereoselective Halogenation in Natural Product Synthesis","volume":"55","author":"Chung","year":"2016","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit4c","doi-asserted-by":"publisher","first-page":"540","DOI":"10.1021\/np800651m","article-title":"Biohalogenation: Nature\u2019s\nWay to Synthesize Halogenated Metabolites","volume":"72","author":"Wagner","year":"2009","journal-title":"J.\nNat. Prod."},{"key":"2026090114525402900_cit4d","doi-asserted-by":"publisher","first-page":"3364","DOI":"10.1021\/cr050313i","article-title":"Nature\u2019s\nInventory of Halogenation Catalysts: Oxidative Strategies Predominate","volume":"106","author":"Vaillancourt","year":"2006","journal-title":"Chem. Rev."},{"key":"2026090114525402900_cit5","doi-asserted-by":"publisher","first-page":"4567","DOI":"10.1021\/cr3004778","article-title":"Tetrahydrofuran-Containing\nMacrolides: A Fascinating Gift from the Deep Sea","volume":"113","author":"Lorente","year":"2013","journal-title":"Chem. Rev."},{"key":"2026090114525402900_cit6","doi-asserted-by":"publisher","first-page":"254","DOI":"10.1002\/tcr.20119","article-title":"Marine Cytotoxic Macrolides\nHaterumalides and Biselides,\nand Related Natural Products","volume":"7","author":"Kigoshi","year":"2007","journal-title":"Chem. Rec."},{"key":"2026090114525402900_cit7","doi-asserted-by":"publisher","first-page":"6309","DOI":"10.1016\/S0040-4039(99)01291-5","article-title":"Isolation and Structures of Haterumalides NA, NB, NC,\nND and NE, Novel Macrolides from an Okinawan Sponge Ircinia sp","volume":"40","author":"Takada","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit8","doi-asserted-by":"publisher","first-page":"957","DOI":"10.1021\/ol0341804","article-title":"Enantioselective\nSynthesis of 15-epi-Haterumalide NA Methyl Ester\nand Revised Structure of Haterumalide NA","volume":"5","author":"Kigoshi","year":"2003","journal-title":"Org.\nLett."},{"key":"2026090114525402900_cit9a","doi-asserted-by":"publisher","first-page":"4385","DOI":"10.1021\/ol0356789","article-title":"Synthesis of ent-Haterumalide NA (ent-Oocydin\nA) Methyl Ester","volume":"5","author":"Gu","year":"2003","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit9b","doi-asserted-by":"publisher","first-page":"6950","DOI":"10.1021\/ja051749i","article-title":"Alkyne Haloallylation [with Pd(II)]\nas a Core Strategy for Macrocycle Synthesis: A Total Synthesis of\n(\u2212)-Haterumalide NA\/(\u2212)-Oocydin A","volume":"127","author":"Hoye","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit9c","doi-asserted-by":"publisher","first-page":"12228","DOI":"10.1021\/ja8043695","article-title":"Total Synthesis of Haterumalide NA and NC via a Chromium-Mediated\nMacrocyclization","volume":"130","author":"Schomaker","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit9d","doi-asserted-by":"publisher","first-page":"3762","DOI":"10.1002\/anie.200800585","article-title":"Total Synthesis of (+)-Oocydin A: Application of the\nSuzuki-Miyaura Cross-Coupling of 1,1-Dichloro-1-alkenes with 9-Alkyl-9-BBN","volume":"47","author":"Roulland","year":"2008","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit9e","doi-asserted-by":"publisher","first-page":"1859","DOI":"10.1021\/ol800554f","article-title":"Second-Generation Total Synthesis\nof Haterumalide NA Using B-Alkyl Suzuki-Miyaura Coupling","volume":"10","author":"Hayakawa","year":"2008","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit9f","doi-asserted-by":"publisher","first-page":"3370","DOI":"10.1021\/jo802806z","article-title":"Total Synthesis and Cytotoxicity\nof Haterumalides NA and B and Their Artifical Analogues","volume":"74","author":"Ueda","year":"2009","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit9g","doi-asserted-by":"publisher","first-page":"2958","DOI":"10.1055\/s-0036-1588169","article-title":"Total Synthesis\nof Bisleide A, A Cytotoxic Macrolide of Marine Origin","volume":"49","author":"Hayakawa","year":"2017","journal-title":"Synthesis"},{"key":"2026090114525402900_cit10a","first-page":"653","article-title":"Laulimalide and Isolaulimalide, New\nPaclitaxel-Like Microtubule-Stabilizing Agents","volume":"59","author":"Mooberry","year":"1999","journal-title":"Cancer Res."},{"key":"2026090114525402900_cit10b","doi-asserted-by":"publisher","first-page":"5979","DOI":"10.1002\/chem.200802605","article-title":"The Laulimalide Family: Total Synthesis and Biological\nEvaluation of Neolaulimalide, Isolaulimalide, Laulimalide and a Nonnatural\nAnalogue","volume":"15","author":"Gollner","year":"2009","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit11a","volume-title":"Circular Dichroic Spectroscopy:\nExciton Coupling in Organic Stereochemistry","author":"Harada","year":"1983"},{"key":"2026090114525402900_cit11b","volume-title":"Organic Conformational\nAnalysis and Stereochemistry from Circular Dichroism Spectroscopy","author":"Lightner","year":"2000"},{"key":"2026090114525402900_cit12a","doi-asserted-by":"publisher","first-page":"451","DOI":"10.1021\/np0605844","article-title":"Bioactive Macrolides\nand Polyketides from Marine Dinoflagellates of the Genus Amphidinium","volume":"70","author":"Kobayashi","year":"2007","journal-title":"J. Nat. Prod."},{"key":"2026090114525402900_cit12b","doi-asserted-by":"publisher","first-page":"329","DOI":"10.1002\/ijch.201100006","article-title":"From Total Synthesis to Diverted\nTotal Synthesis: Case Studies in the Amphidinolide Series","volume":"51","author":"Fu\u0308rstner","year":"2011","journal-title":"Isr. J. Chem."},{"key":"2026090114525402900_cit13a","doi-asserted-by":"publisher","first-page":"9534","DOI":"10.1002\/anie.201301700","article-title":"Total Synthesis\nof Amphidinolide F","volume":"52","author":"Valot","year":"2013","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit13b","doi-asserted-by":"publisher","first-page":"2398","DOI":"10.1002\/chem.201405790","article-title":"Concise Total\nSyntheses of Amphidinoilides C and F","volume":"21","author":"Valot","year":"2015","journal-title":"Chem.\n- Eur. J."},{"key":"2026090114525402900_cit14a","doi-asserted-by":"publisher","first-page":"10792","DOI":"10.1021\/ja404796n","article-title":"Exploiting Hidden\nSymmetry in Natural Products: Total Syntheses of Amphidinolides C\nand F","volume":"135","author":"Mahapatra","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit14b","doi-asserted-by":"publisher","first-page":"3192","DOI":"10.1021\/acs.orglett.8b01020","article-title":"Total Synthesis of the Marine Macrolide Amphidinolide\nF","volume":"20","author":"Ferrie\u0301","year":"2018","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit15","unstructured":"Heinrich, M.\n          \n          Studien zu Chagosensine:\nTotalsynthese der postulierten Struktur & Synthetische Arbeiten\nzur stereochemischen Strukturaufkla\u0308rung, Ph.D. Thesis, TU Dortmund, 2020; 10.17877\/DE290R-20945."},{"key":"2026090114525402900_cit16","doi-asserted-by":"publisher","first-page":"2779","DOI":"10.1055\/s-0031-1289862","article-title":"Various Entries\nto Vinyl Chloride Derivatives and their Application in Total Synthesis\nof Natural Products","volume":"2011","author":"Guinchard","year":"2011","journal-title":"Synlett"},{"key":"2026090114525402900_cit17","doi-asserted-by":"publisher","first-page":"1653","DOI":"10.1021\/ol034284e","article-title":"Mild Procedure for\nthe Catalytic Bis(stannylation)\nof Alkynes with Hexaalkylditins","volume":"5","author":"Mancuso","year":"2003","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit19","doi-asserted-by":"publisher","first-page":"3573","DOI":"10.1016\/S0040-4039(99)00575-4","article-title":"Stereospecific\nStille-Coupling Reaction of (Z)-1,2-Bis(trimethylstannyl)ethenes with\nHypervalent Iodonium Salts","volume":"40","author":"Kang","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit20a","doi-asserted-by":"publisher","first-page":"969","DOI":"10.1016\/0040-4020(89)80009-2","article-title":"Some Chemistry\nof Organotin Synthons containing Two Organotin Moieties","volume":"45","author":"Mitchell","year":"1989","journal-title":"Tetrahedron"},{"key":"2026090114525402900_cit20b","doi-asserted-by":"publisher","first-page":"45","DOI":"10.1016\/S0022-328X(96)06151-7","article-title":"Tin for Organic\nSynthesis. Part 15. The Use of 1,2-Bis(trimethylstannyl)-1-alkenes\nin Electrophilic Destannylation Reactions","volume":"519","author":"Niestroj","year":"1996","journal-title":"J.\nOrganomet. Chem."},{"key":"2026090114525402900_cit20c","doi-asserted-by":"publisher","first-page":"6333","DOI":"10.1016\/0040-4039(91)80162-Y","article-title":"Regio- and Stereocontrolled\nStannylmetallation of 3,3-Diethoxy-prop-1-yne and 4,4-Diethoxy-but-1-yne:\nAn Efficient Access to the Corresponding Vinyltins with Fixed Configurations","volume":"32","author":"Beaudet","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit20d","doi-asserted-by":"publisher","first-page":"1577","DOI":"10.1055\/s-2006-944207","article-title":"Stille\nReactions of 2,3-Bis(stannyl)butenoates: An Unexpected Regioselectivity","volume":"2006","author":"Carter","year":"2006","journal-title":"Synlett"},{"key":"2026090114525402900_cit21a","doi-asserted-by":"publisher","first-page":"4442","DOI":"10.1002\/anie.200500368","article-title":"Palladium-Catalyzed Cross-Coupling Reactions in Total\nSynthesis","volume":"44","author":"Nicolaou","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit21b","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1002\/0471264180.or050.01","article-title":"The Stille Reaction","volume":"50","author":"Farina","year":"1997","journal-title":"Org. React."},{"key":"2026090114525402900_cit22a","doi-asserted-by":"publisher","first-page":"6563","DOI":"10.1016\/0040-4039(91)80222-R","article-title":"The Friedel-Crafts Reaction of 1-(Phenylthio)vinyl\nchlorides","volume":"32","author":"Takeda","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit22b","doi-asserted-by":"publisher","first-page":"92","DOI":"10.1002\/ejoc.200500353","article-title":"The Application\nof [\u03b3-(Silyloxy)allylidene]ditin to the Efficient Synthesis\nof the Chromophore of the Neocarzinostatin Dihydroxycyclopentene-Based\nDienediyne Core","volume":"2006","author":"Madec","year":"2006","journal-title":"Eur. J. Org. Chem."},{"key":"2026090114525402900_cit23","doi-asserted-by":"publisher","first-page":"6241","DOI":"10.1002\/anie.201501608","article-title":"Selective\nFormation of a Trisubstituted Alkene Motif by trans-Hydrostannation\/Stille\nCouling: Application ot the Total Synthesis and Late-Stage Modification\nof 5,6-Dihydrocineromycin B","volume":"54","author":"Rummelt","year":"2015","journal-title":"Angew. Chem., Int.\nEd."},{"key":"2026090114525402900_cit24","doi-asserted-by":"publisher","first-page":"6977","DOI":"10.1021\/acs.joc.7b02871","article-title":"Motif-Oriented\u201c Total Synthesis\nof Nannocystin Ax. Preparation and Biological Assessment of Analogues","volume":"83","author":"Meng","year":"2018","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit25a","doi-asserted-by":"publisher","first-page":"911","DOI":"10.1021\/cr0301402","article-title":"Macrolactonizations\nin the Total Synthesis of Natural Products","volume":"106","author":"Parenty","year":"2006","journal-title":"Chem. Rev."},{"key":"2026090114525402900_cit25b","doi-asserted-by":"publisher","first-page":"PR1","DOI":"10.1021\/cr300129n","article-title":"Update 1 of: Macrolactonizations in the Total Synthesis\nof Natural Products","volume":"113","author":"Parenty","year":"2013","journal-title":"Chem. Rev."},{"key":"2026090114525402900_cit26a","doi-asserted-by":"publisher","first-page":"4510","DOI":"10.1039\/C8CS00027A","article-title":"Recent Advances in Ruthenium-based Olefin Metathesis","volume":"47","author":"Ogba","year":"2018","journal-title":"Chem. Soc. Rev."},{"key":"2026090114525402900_cit26b","doi-asserted-by":"publisher","first-page":"3749","DOI":"10.1055\/s-0037-1610206","article-title":"Recent Advances in Total Synthesis\nvia Metathesis Reactions","volume":"50","author":"Cheng-Sanchez","year":"2018","journal-title":"Synthesis"},{"key":"2026090114525402900_cit26c","doi-asserted-by":"publisher","first-page":"6505","DOI":"10.1039\/c1cc10464k","article-title":"Metathesis in Total Synthesis","volume":"47","author":"Fu\u0308rstner","year":"2011","journal-title":"Chem. Commun."},{"key":"2026090114525402900_cit26d","doi-asserted-by":"publisher","first-page":"243","DOI":"10.1038\/nature06351","article-title":"The Remarkable Metal-catalyzed Olefin\nMetathesis Reaction","volume":"450","author":"Hoveyda","year":"2007","journal-title":"Nature"},{"key":"2026090114525402900_cit26e","doi-asserted-by":"publisher","first-page":"4490","DOI":"10.1002\/anie.200500369","volume":"44","author":"Nicolaou","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit26f","doi-asserted-by":"publisher","first-page":"3012","DOI":"10.1002\/1521-3773(20000901)39:17&lt;3012::AID-ANIE3012&gt;3.0.CO;2-G","article-title":"Olefin Metathesis and Beyond","volume":"39","author":"Fu\u0308rstner","year":"2000","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit27a","doi-asserted-by":"publisher","first-page":"2794","DOI":"10.1002\/anie.201204513","article-title":"Alkyne Metathesis on\nthe Rise","volume":"52","author":"Fu\u0308rstner","year":"2013","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit27b","doi-asserted-by":"publisher","first-page":"1229713","DOI":"10.1126\/science.1229713","article-title":"Teaching Metathesis \u201cSimple\u201d\nStereochemistry","volume":"341","author":"Fu\u0308rstner","year":"2013","journal-title":"Science"},{"key":"2026090114525402900_cit28a","doi-asserted-by":"publisher","first-page":"3969","DOI":"10.1016\/S0040-4039(00)88238-6","article-title":"Dimethylboron\nbromide and Diphenylboron bromide. Acetal and Ketal Cleavage. Cleavage\nof MEM, MOM and MTM Ethers","volume":"24","author":"Quindon","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit28b","doi-asserted-by":"publisher","first-page":"3912","DOI":"10.1021\/jo00195a007","article-title":"Dimethylboron bromide\nand Diphenylboron bromide: Cleavage of Acetals and Ketals","volume":"49","author":"Guindon","year":"1984","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit29a","doi-asserted-by":"publisher","first-page":"15719","DOI":"10.1021\/ja508846g","article-title":"Synthesis,\nMolecular Editing and Biological Assessment of the Potent Cytotoxin\nLeiodermatolide","volume":"136","author":"Mailhol","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit29b","doi-asserted-by":"publisher","first-page":"219","DOI":"10.1002\/chem.201404873","article-title":"A New Method\nfor the Preparation of Non-Terminal Alkynes. Application to the Total\nSynthesis of Tulearin A and C","volume":"21","author":"Lehr","year":"2015","journal-title":"Chem. - Eur.\nJ."},{"key":"2026090114525402900_cit31","doi-asserted-by":"publisher","first-page":"5640","DOI":"10.1021\/jo980112x","article-title":"Regioselective Catalytic Dehydrogenation of Aldehydes\nand Ketones","volume":"63","author":"Shvo","year":"1998","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit32","doi-asserted-by":"publisher","first-page":"4926","DOI":"10.1002\/anie.201402010","article-title":"Heterocycle\nSynthesis Based on Allylic Alcohol Transposition\nUsing Traceless Trapping Groups","volume":"53","author":"Xie","year":"2014","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090114525402900_cit33","doi-asserted-by":"publisher","first-page":"2743","DOI":"10.1039\/p19930002743","article-title":"Synthesis of Medium Ring Ethers.\nPart 4. Stereoselective Claisen-mediated Ring Expansion as a Route\nto Homochiral Disubstituted Medium Ring Lactones","author":"Fuhry","year":"1993","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"2026090114525402900_cit34a","doi-asserted-by":"publisher","first-page":"1191","DOI":"10.1021\/cr980379w","article-title":"Around and Beyond Cram\u2019s\nRule","volume":"99","author":"Mengel","year":"1999","journal-title":"Chem. Rev."},{"key":"2026090114525402900_cit34b","doi-asserted-by":"publisher","first-page":"556","DOI":"10.1002\/anie.198405561","article-title":"Chelation or Non-Chelation Control in Addition Reactions\nof Chiral \u03b1- and \u03b2- Alkoxy Carbonyl Compounds","volume":"23","author":"Reetz","year":"1984","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"2026090114525402900_cit36a","doi-asserted-by":"publisher","first-page":"67","DOI":"10.1246\/cl.1990.67","article-title":"A Convenient\nMethod for the Stereoselective Preparation of trans-2-Hydroxymethyltetrahydrofurans by the Oxidative Cyclization of\n5-Hydroxy-1-alkenes with Molecular Oxygen Catalyzed by Cobalt(II)\nComplex","volume":"19","author":"Inoki","year":"1990","journal-title":"Chem. Lett."},{"key":"2026090114525402900_cit36b","doi-asserted-by":"publisher","first-page":"17","DOI":"10.1246\/bcsj.68.17","article-title":"Recent Advances in Aerobic Oxygenation","volume":"68","author":"Mukaiyama","year":"1995","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2026090114525402900_cit37a","doi-asserted-by":"publisher","first-page":"3532","DOI":"10.1039\/b804588g","article-title":"Activation\nof Molecular Oxygen and\nits Use in Stereoselective Tetrahydrofuran-Syntheses from \u03b4,\u03b5-Unsaturated\nAlcohols","volume":"6","author":"Mene\u0301ndez Pe\u0301rez","year":"2008","journal-title":"Org. Biomol. Chem."},{"key":"2026090114525402900_cit37b","doi-asserted-by":"publisher","first-page":"12918","DOI":"10.1021\/ja904577c","article-title":"Reductive and Brominative\nTerminatioin of Alkenol Cyclization in Aerobic Cobalt-Catalyzed Reactions","volume":"131","author":"Schuch","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit38a","doi-asserted-by":"publisher","first-page":"847","DOI":"10.1055\/s-0039-1690730","article-title":"Gram-Scale Synthesis of the Co(nmp)2 Catalyst\nto Prepare trans-2,5-Disubstituted Tetrahydrofurans\nby the Aerobic Oxidative Cyclization of Pent-4-en-1-ols","volume":"52","author":"Morra","year":"2020","journal-title":"Synthesis"},{"key":"2026090114525402900_cit38b","doi-asserted-by":"publisher","first-page":"756","DOI":"10.1002\/ejoc.201201331","article-title":"BF2OBn\u00b7OEt2: A Lewis Acid, Its Use in a Regio- and Stereoselective Opening of\nTrisubstituted Epoxides, and Its Application towards Amphidinolide\nC and F","volume":"2013","author":"Morra","year":"2013","journal-title":"Eur. J. Org. Chem."},{"key":"2026090114525402900_cit39","doi-asserted-by":"publisher","first-page":"8632","DOI":"10.1016\/j.tet.2013.07.026","article-title":"Gram Scale\nSynthesis of the C(1)-C(9) Fragment of Amphidinolide\nC","volume":"69","author":"Morra","year":"2013","journal-title":"Tetrahedron"},{"key":"2026090114525402900_cit40","doi-asserted-by":"publisher","first-page":"7694","DOI":"10.1021\/acs.joc.8b00575","article-title":"Cobalt-Catalyzed\nStereoselective Synthesis of 2,5-trans-THF Nitrile\nDerivatives as a Platform for Diversification: Development and Mechanistic\nStudies","volume":"83","author":"Ali","year":"2018","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit41","doi-asserted-by":"publisher","first-page":"5505","DOI":"10.1021\/ja00997a067","article-title":"Sulfur Trioxide\nin the Oxidation of Alcohols by Dimethyl\nSulfoxide","volume":"89","author":"Parikh","year":"1967","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit42a","doi-asserted-by":"publisher","first-page":"9274","DOI":"10.1021\/jo034964v","article-title":"Leucascandrolide\nA: Synthesis and Related Studies","volume":"68","author":"Fettes","year":"2003","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit42b","doi-asserted-by":"publisher","first-page":"9284","DOI":"10.1021\/jo501733m","article-title":"Total Synthesis of (+)-18-epi-Latrunculol A: Development of a Synthetic Route","volume":"79","author":"Williams","year":"2014","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit43a","doi-asserted-by":"publisher","first-page":"1019","DOI":"10.1246\/cl.1990.1019","article-title":"Facile Synthesis\nof Optically Active anti-\u03b1,\u03b2-Dihydroxy\nEster Derivatives","volume":"19","author":"Mukaiyama","year":"1990","journal-title":"Chem. Lett."},{"key":"2026090114525402900_cit43b","doi-asserted-by":"publisher","first-page":"1708","DOI":"10.1246\/bcsj.67.1708","article-title":"Diastereo-\nand Enantioselective Synthesis of syn- and anti-1,2-Diol Units by Asymmetric\nAldol Reactions","volume":"67","author":"Mukaiyama","year":"1994","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2026090114525402900_cit43c","doi-asserted-by":"publisher","first-page":"144","DOI":"10.1002\/tcr.201300022","article-title":"Asymmetric Mukaiyama Aldol Reactions Using Chiral Diamine\u2013Coordinated\nSn(II) Triflate: Development and Application to Natural Product Synthesis","volume":"14","author":"Shiina","year":"2014","journal-title":"Chem. Rec."},{"key":"2026090114525402900_cit44a","doi-asserted-by":"publisher","first-page":"95","DOI":"10.2183\/pjab.73.95","article-title":"Assymetric\nTotal Synthesis of Taxol","volume":"73B","author":"Mukaiyama","year":"1997","journal-title":"Proc. Jpn. Acad.,\nSer. B"},{"key":"2026090114525402900_cit44b","doi-asserted-by":"publisher","first-page":"8451","DOI":"10.1021\/ja00071a066","article-title":"Total Synthesis of\n(+)-Leinamycin","volume":"115","author":"Kanda","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit45","doi-asserted-by":"publisher","first-page":"3173","DOI":"10.1016\/0040-4039(95)00505-7","article-title":"Molecular\nRecognition by Artificial\nChiral Catalysts Utilizing a Metal Chelate. A Remarkable Difference\nin Reactivity Between Geometrical Isomers of Silyl Enolates in Asymmetric\nAldol Reactions Using Chiral Tin(II) Catalysts","volume":"36","author":"Kobayashi","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit46","doi-asserted-by":"publisher","first-page":"7050","DOI":"10.1021\/ja00175a043","article-title":"Facile Reduction of\nEthyl Thiol Esters\nto Aldehydes: Application to a Total Synthesis of (+)-Neothramycin\nA Methyl Ether","volume":"112","author":"Fukuyama","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit47","doi-asserted-by":"publisher","first-page":"2173","DOI":"10.1016\/S0040-4039(00)99640-0","article-title":"A Stereoselective Synthesis\nof (Z)-1-Iodo-1-alkenes","volume":"30","author":"Stork","year":"1989","journal-title":"Tetrahedron\nLett."},{"key":"2026090114525402900_cit48a","doi-asserted-by":"publisher","first-page":"2993","DOI":"10.1021\/ol026401w","article-title":"Trans-Hydrometalation of Alkynes by\na Combination of InCl3 and DIBAL-H: One-Pot Access to Functionalized (Z)-Alkenes","volume":"4","author":"Takami","year":"2002","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit48b","doi-asserted-by":"publisher","first-page":"6627","DOI":"10.1021\/jo0344790","article-title":"Triethylborane-Mediated Hydrogallation\nand Hydroindation: Novel Access to Organogalliums and Organoindiums","volume":"68","author":"Takami","year":"2003","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit49a","doi-asserted-by":"publisher","first-page":"1484","DOI":"10.1021\/acs.joc.5b02595","article-title":"Stereocontrolled Synthesis\nof a Possible Stereoisomer of Laurenidificin and a Formal Total Synthesis\nof (+)-Aplysiallene Featuring a Stereospecific Ring Contraction","volume":"81","author":"Kobayashi","year":"2016","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit49b","doi-asserted-by":"publisher","first-page":"13826","DOI":"10.1002\/anie.201409038","article-title":"A Cascade Strategy Enables a Total\nSynthesis of (\u2212)-Gephyrotoxin","volume":"53","author":"Chu","year":"2014","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026090114525402900_cit49c","doi-asserted-by":"publisher","first-page":"544","DOI":"10.1021\/ol203162s","article-title":"Remarkable Stereoselectivity in Intramolecular\nBorono-Mannich Reactions: Synthesis of Conduramines","volume":"14","author":"Norsikian","year":"2012","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit49d","doi-asserted-by":"publisher","first-page":"7437","DOI":"10.1021\/acs.joc.7b01115","article-title":"Total Synthesis of Pestalotioprolide G and Putative\nStructure of Pestalotioprolide H","volume":"82","author":"Paul","year":"2017","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit50a","doi-asserted-by":"publisher","first-page":"3600","DOI":"10.1002\/1521-3773(20011001)40:19&lt;3600::AID-ANIE3600&gt;3.0.CO;2-N","article-title":"Nickel-Catalyzed Homoallylation of Aldehydes in the\nPresence of Water and Alcohols","volume":"40","author":"Kimura","year":"2001","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090114525402900_cit50b","doi-asserted-by":"publisher","first-page":"2954","DOI":"10.1021\/ol100959a","article-title":"A Formal Synthesis\nof the C1\u2013C9 Fragment of Amphidinolide C Employing the Tamaru\nReaction","volume":"12","author":"Paudyal","year":"2010","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit51","doi-asserted-by":"publisher","first-page":"3788","DOI":"10.5012\/bkcs.2010.31.12.3788","article-title":"Facile\nand Large Scale Synthesis\nof Diverse 4-O-Protected 2,3-O-Isopropylidene-D-erythrose","volume":"31","author":"Bepary","year":"2010","journal-title":"Bull. Korean Chem. Soc."},{"key":"2026090114525402900_cit52a","doi-asserted-by":"publisher","first-page":"4033","DOI":"10.1021\/ja973847c","article-title":"Novel and Highly Regio- and Stereoselective Nickel-Catalyzed\nHomoallylation of Benzaldehyde with 1,3-Dienes","volume":"120","author":"Kimura","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit52b","doi-asserted-by":"publisher","first-page":"397","DOI":"10.1002\/(SICI)1521-3773(19990201)38:3&lt;397::AID-ANIE397&gt;3.0.CO;2-Y","article-title":"Nickel-Catalyzed Homoallylation of\nAldehydes and Ketones with 1,3-Dienes and Complementary Promotion\nby Diethylzinc or Triethylborane","volume":"38","author":"Kimura","year":"1999","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090114525402900_cit53","doi-asserted-by":"publisher","first-page":"8559","DOI":"10.1021\/ja0608904","article-title":"Regio- and\nStereoselective Nickel-Catalyzed Homoallylation of Aldehydes with\n1,3-Dienes","volume":"128","author":"Kimura","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit54","doi-asserted-by":"publisher","first-page":"1621","DOI":"10.1021\/ol050350w","article-title":"Kinetic Study of Various\nPhosphoramidite Ligands in\nthe Iridium-Catalyzed Allylic Substitution","volume":"7","author":"Polet","year":"2005","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit55","doi-asserted-by":"publisher","first-page":"127","DOI":"10.1002\/0471264180.os063.14","article-title":"2,3-O-Isopropylidene-D-erythrono-lactone","volume":"63","author":"Cohen","year":"2003","journal-title":"Org. Synth."},{"key":"2026090114525402900_cit56","doi-asserted-by":"publisher","first-page":"485","DOI":"10.1002\/0471264180.os060.10","article-title":"Diels-Alder Reaction of 1,2,4,5-Hexatetraene:\nTetramethyl[2.2]paracyclophane-4,5,12,13-tetracarboxylate","volume":"60","author":"Hopf","year":"2003","journal-title":"Org. Synth."},{"key":"2026090114525402900_cit57","doi-asserted-by":"publisher","first-page":"247","DOI":"10.1016\/0022-328X(93)80406-2","article-title":"Efficient\nPalladium Catalysts for\nthe Carbonylation of Alkynes","volume":"455","author":"Drent","year":"1993","journal-title":"J. Organomet.\nChem."},{"key":"2026090114525402900_cit58a","doi-asserted-by":"publisher","first-page":"13923","DOI":"10.1002\/chem.201403983","article-title":"Mechanism of Alkyne Alkoxycarbonylation\nat a Pd Catalyst with P,N Hemilabile Ligands: A Density Functional\nStudy","volume":"20","author":"Crawford","year":"2014","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit58b","doi-asserted-by":"publisher","first-page":"8543","DOI":"10.1039\/C9CP01471C","article-title":"Palladium-Catalyzed\nAlkyne Alkoxycarbonylation with P,N-chelating Ligands Revisited: A\nDensity Functional Theory Study","volume":"21","author":"Ahmad","year":"2019","journal-title":"Phys. Chem.\nChem. Phys."},{"key":"2026090114525402900_cit59a","doi-asserted-by":"publisher","first-page":"28","DOI":"10.1002\/cctc.200900062","article-title":"Palladium-Catalyzed\nCarbonylation Reactions of Alkenes and Alkynes","volume":"1","author":"Brennfu\u0308hrer","year":"2009","journal-title":"ChemCatChem"},{"key":"2026090114525402900_cit59b","doi-asserted-by":"publisher","first-page":"2634","DOI":"10.1016\/j.tetlet.2015.04.043","article-title":"Metal-catalyzed Carbonylation of\nAlkynes: Key Aspects and Recent Development","volume":"56","author":"Quintero-Duque","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit60","doi-asserted-by":"publisher","first-page":"8494","DOI":"10.1002\/chem.201601163","article-title":"A Two-Component Alkyne Metathesis Catalyst System with\nan Improved Substrate Scope and Functional Group Tolerance: Development\nand Applications to Natural Product Synthesis","volume":"22","author":"Schaubach","year":"2016","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit61a","doi-asserted-by":"publisher","first-page":"561","DOI":"10.1016\/j.drudis.2012.01.013","article-title":"Natural and Synthetic \u03b1-Methylenelactones\nand \u03b1-Methylenelactams with Anticancer Potential","volume":"17","author":"Janecka","year":"2012","journal-title":"Drug Discovery Today"},{"key":"2026090114525402900_cit61b","doi-asserted-by":"publisher","first-page":"94","DOI":"10.1002\/anie.198500941","article-title":"Synthesis and Biological Activity\nof \u03b1-Methylene-\u03b3-butyrolactones","volume":"24","author":"Hoffmann","year":"1985","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"2026090114525402900_cit62a","doi-asserted-by":"publisher","first-page":"4976","DOI":"10.1021\/ol1021228","article-title":"Efficient\nSynthesis of the C(1)\u2013C(9) Fragment of Amphidinolides C, C2,\nand F","volume":"12","author":"Ferrie\u0301","year":"2010","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit62b","doi-asserted-by":"publisher","first-page":"1178","DOI":"10.1021\/ol303515h","article-title":"Syntheses of the C1\u2013C14 and\nC15\u2013C25 Fragments of Amphidinolide C","volume":"15","author":"Wu","year":"2013","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit64","doi-asserted-by":"publisher","first-page":"7061","DOI":"10.1021\/ja020238i","article-title":"Total Syntheses\nof the Phytotoxic Lactones Herbarumin\nI and II and a Synthesis-based Solution of the Pinolidoxin Puzzle","volume":"124","author":"Fu\u0308rstner","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit65","doi-asserted-by":"publisher","first-page":"5161","DOI":"10.1016\/S0040-4039(99)00956-9","article-title":"Selective oxidation\nof primary silyl ethers and its application to the synthesis of natural\nproducts","volume":"40","author":"Rodri\u0301guez","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"2026090114525402900_cit66a","doi-asserted-by":"publisher","first-page":"561","DOI":"10.1080\/00397918908050700","article-title":"Methanolysis of Dimethyl (1-Diazo-2-oxopropyl)\nPhosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and\nReaction with Carbonyl Compounds","volume":"19","author":"Ohira","year":"1989","journal-title":"Synth. Commun."},{"key":"2026090114525402900_cit66b","doi-asserted-by":"publisher","first-page":"521","DOI":"10.1055\/s-1996-5474","article-title":"An Improved One-pot Procedure for the Synthesis of\nAlkynes from Aldehydes","volume":"1996","author":"Mu\u0308ller","year":"1996","journal-title":"Synlett"},{"key":"2026090114525402900_cit67a","doi-asserted-by":"publisher","first-page":"15433","DOI":"10.1021\/ja0304953","article-title":"Total Synthesis of Apoptolidin: Construction\nof Enantiomerically Pure Fragments","volume":"125","author":"Nicolaou","year":"2003","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026090114525402900_cit67b","doi-asserted-by":"publisher","first-page":"4217","DOI":"10.1002\/anie.201400605","article-title":"Catalysis-based\nTotal Synthesis of Putative Mandelalide A","volume":"53","author":"Willwacher","year":"2014","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026090114525402900_cit67c","doi-asserted-by":"publisher","first-page":"10416","DOI":"10.1002\/chem.201501491","article-title":"Total Synthesis, Stereochemical Revision, and Biological\nReassessment of Mandelalide A: Chemical Mimicry of Interfamily Relationships","volume":"21","author":"Willwacher","year":"2015","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit67d","doi-asserted-by":"publisher","first-page":"255","DOI":"10.1002\/chem.201804988","article-title":"Total Synthesis\nof Callyspongiolide, Part 2: The Ynoate Metathesis\/cis-Reduction Strategy","volume":"25","author":"Wo\u0308lfl","year":"2019","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit68","doi-asserted-by":"publisher","first-page":"3295","DOI":"10.1021\/acs.orglett.9b01024","article-title":"Alkynylation of Pentose Derivatives\nwith Stereochemical Fidelity: Implications for the Regioselectivity\nof Alkynyl Diol Cycloisomerizations to Cyclic Enol Ethers","volume":"21","author":"McDonald","year":"2019","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit70","doi-asserted-by":"publisher","first-page":"1555","DOI":"10.1021\/ar800148f","article-title":"The Development\nof Versatile Methods for Palladium-Catalyzed Coupling Reactions of\nAryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands","volume":"41","author":"Fu","year":"2008","journal-title":"Acc.\nChem. Res."},{"key":"2026090114525402900_cit71","doi-asserted-by":"publisher","first-page":"12376","DOI":"10.1021\/ja9726926","article-title":"Sulfonium\nSalts. Participants par Excellence in Metal-Catalyzed\nCarbon\u2013Carbon Bond-Forming\nReactions","volume":"119","author":"Srogl","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit72","doi-asserted-by":"publisher","first-page":"2873","DOI":"10.1039\/b805299a","article-title":"A Versatile Protocol\nfor Stille-Migita Cross Coupling Reactions","author":"Fu\u0308rstner","year":"2008","journal-title":"Chem. Commun."},{"key":"2026090114525402900_cit73","doi-asserted-by":"publisher","first-page":"1989","DOI":"10.1246\/bcsj.52.1989","article-title":"A Rapid Esterification\nby Means of Mixed Anhydride and Its Application to Large-ring Lactonization","volume":"52","author":"Inanaga","year":"1979","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2026090114525402900_cit74","doi-asserted-by":"publisher","first-page":"2091","DOI":"10.1016\/S0040-4020(01)97963-3","article-title":"Oxidation of \u03b1,\u03b2-Unsaturated\nAldehydes","volume":"37","author":"Bal","year":"1981","journal-title":"Tetrahedron"},{"key":"2026090114525402900_cit77","doi-asserted-by":"publisher","first-page":"3734","DOI":"10.1021\/jo00092a045","article-title":"Amphidinolide\nI, a New Cytotoxic\n27-Membered Macrolide from the Cultured Dinoflagellate Amphidinium sp","volume":"59","author":"Tsuda","year":"1994","journal-title":"J. Org. Chem."},{"key":"2026090114525402900_cit79","doi-asserted-by":"publisher","first-page":"6203","DOI":"10.1021\/ja00436a023","article-title":"Favorskii-Type Ring Contraction in Bicyclic Chloro\nKetones. A Stereochemistry- and Medium-Dependent Photochemical Solvolysis","volume":"98","author":"Jones","year":"1976","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit80a","doi-asserted-by":"publisher","first-page":"1012","DOI":"10.1002\/anie.200460864","article-title":"Chasing\nMolecules That Were Never There: Misassigned Natural Products and\nthe Role of Chemical Synthesis in Modern Structure Elucidation","volume":"44","author":"Nicolaou","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit80b","doi-asserted-by":"publisher","first-page":"1105","DOI":"10.1039\/b809658a","article-title":"Structural Revisions of Natural Products by Total Synthesis","volume":"26","author":"Maier","year":"2009","journal-title":"Nat. Prod. Rep."},{"key":"2026090114525402900_cit81a","doi-asserted-by":"publisher","first-page":"304","DOI":"10.1002\/anie.201005850","article-title":"The Leiodolide\nB Puzzle","volume":"50","author":"Larive\u0301e","year":"2011","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit81b","doi-asserted-by":"publisher","first-page":"8450","DOI":"10.1002\/anie.200803339","article-title":"A Synthesis-Driven Structure Revision\nof Berkelic Acid Methyl Ester","volume":"47","author":"Buchgraber","year":"2008","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090114525402900_cit81c","doi-asserted-by":"publisher","first-page":"3983","DOI":"10.1002\/chem.200802067","article-title":"Total Syntheses of Amphidinolides B1, B4, G1, H1 and\nStructure Revision of Amphidinolide H2","volume":"15","author":"Fu\u0308rstner","year":"2009","journal-title":"Chem.\n- Eur. J."},{"key":"2026090114525402900_cit81d","doi-asserted-by":"publisher","first-page":"13132","DOI":"10.1021\/ja036521e","article-title":"Structure\nAssignment, Total Synthesis and Antiviral Evaluation of Cycloviracin\nB1","volume":"125","author":"Fu\u0308rstner","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"2026090114525402900_cit81e","doi-asserted-by":"publisher","first-page":"7525","DOI":"10.1002\/anie.201702189","article-title":"Polyunsaturated C-Glycosidic 4-Hydroxy-2-pyrone Derivatives:\nTotal Synthesis Shows that Putative Orevactaene is Likely Identical\nwith Epipyrone A","volume":"56","author":"Preindl","year":"2017","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090114525402900_cit81f","doi-asserted-by":"publisher","first-page":"10712","DOI":"10.1002\/anie.201805125","article-title":"Total Synthesis of Belizentrin Methyl\nEster: Report on a Likely Conquest","volume":"57","author":"Anderl","year":"2018","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026090114525402900_cit82a","doi-asserted-by":"publisher","first-page":"7731","DOI":"10.1002\/chem.201300827","article-title":"Total Synthesis\nof Nominal Gobienine A","volume":"19","author":"Kondoh","year":"2013","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit82b","doi-asserted-by":"publisher","first-page":"2476","DOI":"10.1021\/ol2007296","article-title":"Synthetic\nStudies on Lytophilippine A: Synthesis of the Proposed Structure","volume":"13","author":"Jang","year":"2011","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit82c","doi-asserted-by":"publisher","first-page":"2421","DOI":"10.1021\/acs.orglett.9b00722","article-title":"Synthesis\nof a Diastereomer of the Marine Macrolide Lytophilippine A","volume":"21","author":"Klu\u0308ppel","year":"2019","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit82d","doi-asserted-by":"publisher","first-page":"7423","DOI":"10.1002\/chem.201204545","article-title":"Total Synthesis of the Postulated\nStructure of Fulicineroside","volume":"19","author":"Bartholoma\u0308us","year":"2013","journal-title":"Chem. - Eur. J."},{"key":"2026090114525402900_cit82e","doi-asserted-by":"publisher","first-page":"4698","DOI":"10.1021\/ol302074h","article-title":"Asymmetric Catalytic Synthesis of\nthe Proposed Structure of Trocheliophorolide B","volume":"14","author":"Trost","year":"2012","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit82f","doi-asserted-by":"publisher","first-page":"7414","DOI":"10.1002\/ejoc.201101209","article-title":"Total Synthesis of the Proposed Structure of Trocheliophorolide D","volume":"2011","author":"Hwang","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"2026090114525402900_cit82g","doi-asserted-by":"publisher","first-page":"2831","DOI":"10.1021\/ol0609661","article-title":"Synthesis of Nonactin and the Proposed Structure of\nTrilactone","volume":"8","author":"Wu","year":"2006","journal-title":"Org. Lett."},{"key":"2026090114525402900_cit83","doi-asserted-by":"publisher","first-page":"179","DOI":"10.1002\/ijch.201600087","article-title":"The Evolution and Impact\nof Total Synthesis on Chemistry, Biology\nand Medicine","volume":"57","author":"Nicolaou","year":"2017","journal-title":"Isr. J. Chem."}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.0c01700","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/142\/13\/6409\/67500154\/jacs.0c01700.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/142\/13\/6409\/67500154\/jacs.0c01700.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T18:53:04Z","timestamp":1788288784000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/142\/13\/6409\/611021\/Chagosensine-A-Riddle-Wrapped-in-a-Mystery-Inside"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,3,6]]},"references-count":141,"journal-issue":{"issue":"13","published-online":{"date-parts":[[2020,3,6]]},"published-print":{"date-parts":[[2020,4,1]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.0c01700","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,3,6]]}}}