{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T19:45:00Z","timestamp":1792784700815,"version":"4.5.0"},"reference-count":38,"publisher":"American Chemical Society (ACS)","issue":"41","license":[{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100016545","name":"Roche Diagnostics","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100016545","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000062","name":"National Institute of Diabetes and Digestive and Kidney Diseases","doi-asserted-by":"publisher","award":["TL1 DK136047"],"award-info":[{"award-number":["TL1 DK136047"]}],"id":[{"id":"10.13039\/100000062","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["GM119426"],"award-info":[{"award-number":["GM119426"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Atlanta Chapter, Achievement Rewards for College Scientists Foundation","id":[{"id":"https:\/\/ror.org\/054awkm93","id-type":"ROR","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We report our efforts toward the convergent total synthesis of the cembranoid diterpene (\u2212)-knightol, a marine natural product reported to exhibit antibiofilm activity against Staphylococcus aureus, and a rationally designed aryl analog, mknightol. Our strategy was guided by a two-phase approach involving construction of the macrocyclic framework, followed by selective epoxidation and further diversification. Both targets were designed to arise from common western fragment building blocks and an eastern fragment accessible on a gram scale. A scalable cross-electrophile coupling provided efficient access to an advanced intermediate en route to the cyclophane and enabled evaluation of key late-stage transformations.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01838","type":"journal-article","created":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T13:02:41Z","timestamp":1790773361000},"page":"13793-13799","source":"Crossref","is-referenced-by-count":0,"title":["The Convergent Synthetic\nEfforts toward Knightol and\na Simplified Analog"],"prefix":"10.1021","volume":"91","author":[{"given":"Learnmore","family":"Jeremia","sequence":"first","affiliation":[{"name":"Emory University , , , ,","place":["Atlanta, Georgia, United States, 30322"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elise L.","family":"Bezold","sequence":"additional","affiliation":[{"name":"Emory University , , , ,","place":["Atlanta, Georgia, United States, 30322"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kate","family":"Bright","sequence":"additional","affiliation":[{"name":"Emory University , , , ,","place":["Atlanta, Georgia, United States, 30322"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5198-7744","authenticated-orcid":true,"given":"William M.","family":"Wuest","sequence":"additional","affiliation":[{"name":"Emory University , , , ,","place":["Atlanta, Georgia, United States, 30322"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,30]]},"reference":[{"issue":"9","key":"2026101608084859300_cit1","doi-asserted-by":"publisher","first-page":"1595","DOI":"10.1021\/np9002492","article-title":"Cembranoid Diterpenes\nfrom the Caribbean Sea Whip Eunicea Knighti","volume":"72","author":"Tello","year":"2009","journal-title":"J. Nat. Prod."},{"issue":"9","key":"2026101608084859300_cit2","doi-asserted-by":"publisher","first-page":"1637","DOI":"10.1021\/np300313k","article-title":"Disruption\nin Quorum-Sensing Systems and Bacterial Biofilm Inhibition by Cembranoid\nDiterpenes Isolated from the Octocoral Eunicea Knighti","volume":"75","author":"Tello","year":"2012","journal-title":"J. Nat. Prod."},{"issue":"35","key":"2026101608084859300_cit3","doi-asserted-by":"publisher","first-page":"12120","DOI":"10.1021\/acs.joc.6c01571","article-title":"Total Synthesis\nand Biofilm Inhibitory\nStudies of Knightine Cembranoid Diterpenes","volume":"91","author":"Jeremia","year":"2026","journal-title":"J. Org. Chem."},{"issue":"21","key":"2026101608084859300_cit4","doi-asserted-by":"publisher","first-page":"7188","DOI":"10.1021\/jacs.7b03879","article-title":"Diverted Total Synthesis\nof Carolacton-Inspired Analogs Yields Three Distinct Phenotypes in\nStreptococcus Mutans Biofilms","volume":"139","author":"Solinski","year":"2017","journal-title":"J. Am. Chem.\nSoc."},{"issue":"8","key":"2026101608084859300_cit5","doi-asserted-by":"publisher","first-page":"1480","DOI":"10.1021\/acsinfecdis.9b00213","article-title":"Synthetic Simplification\nof Carolacton Enables Chemical Genetic Studies in Streptococcus Mutans","volume":"5","author":"Solinski","year":"2019","journal-title":"ACS Infect. Dis."},{"issue":"4","key":"2026101608084859300_cit6","doi-asserted-by":"publisher","first-page":"1126","DOI":"10.1021\/acs.orglett.8b00054","article-title":"Diverted Total Synthesis\nof the Baulamycins and Analogues Reveals an Alternate Mechanism of\nAction","volume":"20","author":"Steele","year":"2018","journal-title":"Org. Lett."},{"issue":"31","key":"2026101608084859300_cit7","doi-asserted-by":"publisher","first-page":"15080","DOI":"10.1039\/D6SC04046B","article-title":"Concise\nSynthesis of Simplified Aogacillin Analogs Reveals Innate Reactivity\nand Synergy with Aminoglycosides","volume":"17","author":"LeBlanc","year":"2026","journal-title":"Chem. Sci."},{"issue":"2","key":"2026101608084859300_cit8","doi-asserted-by":"publisher","first-page":"298","DOI":"10.1039\/b705660p","article-title":"The Chemistry\nof Marine Furanocembranoids, Pseudopteranes,\nGersolanes, and Related Natural Products","volume":"25","author":"Roethle","year":"2008","journal-title":"Nat.\nProd. Rep."},{"issue":"22","key":"2026101608084859300_cit9","doi-asserted-by":"publisher","first-page":"2267","DOI":"10.1016\/S0040-4039(00)81900-0","article-title":"Synthesis of (\u00b1)-Asperdiol,\na Marine Anticancer Cembrenoid","volume":"24","author":"Aoki","year":"1983","journal-title":"Tetrahedron\nLett."},{"issue":"20","key":"2026101608084859300_cit10","doi-asserted-by":"publisher","first-page":"6389","DOI":"10.1021\/ja00280a046","article-title":"Total Synthesis of (\u2212)-Asperdiol","volume":"108","author":"Tius","year":"1986","journal-title":"J.\nAm. Chem. Soc."},{"issue":"24","key":"2026101608084859300_cit11","doi-asserted-by":"publisher","first-page":"4785","DOI":"10.1021\/jo00172a070","article-title":"Synthesis of Asperdiol","volume":"48","author":"Still","year":"1983","journal-title":"J. Org.\nChem."},{"issue":"6","key":"2026101608084859300_cit12","doi-asserted-by":"publisher","first-page":"858","DOI":"10.1021\/jo00356a021","article-title":"Synthesis of 7(8)-Desoxyasperdiol. A Precursor of the\nCembranoid Asperdiol","volume":"51","author":"Marshall","year":"1986","journal-title":"J. Org. Chem."},{"issue":"17","key":"2026101608084859300_cit13","doi-asserted-by":"publisher","first-page":"3860","DOI":"10.1021\/jo00226a026","article-title":"Synthesis\nof Cembrane Natural Products\nvia [2,3] Wittig Ring Contraction of Propargylic Ethers","volume":"52","author":"Marshall","year":"1987","journal-title":"J. Org. Chem."},{"issue":"5","key":"2026101608084859300_cit14","doi-asserted-by":"publisher","first-page":"1035","DOI":"10.1021\/ja00265a032","article-title":"Total Synthesis\nof (+)-Desepoxyasperdiol","volume":"108","author":"Tius","year":"1986","journal-title":"J. Am. Chem. Soc."},{"issue":"17","key":"2026101608084859300_cit15","doi-asserted-by":"publisher","first-page":"10564","DOI":"10.1021\/acs.joc.8b01383","article-title":"Total Syntheses of (+)-\u03b1-Allokainic Acid and\n(\u2212)-2- Epi-\u03b1-Allokainic Acid Employing Ketopinic Amide\nas a Chiral Auxiliary","volume":"83","author":"Liang","year":"2018","journal-title":"J. Org. Chem."},{"issue":"11","key":"2026101608084859300_cit16","doi-asserted-by":"publisher","first-page":"1617","DOI":"10.1021\/ol0157609","article-title":"Olefin Metathesis in the Design and\nSynthesis of a Globally Constrained Grb2 SH2 Domain Inhibitor","volume":"3","author":"Gao","year":"2001","journal-title":"Org. Lett."},{"issue":"14","key":"2026101608084859300_cit17","doi-asserted-by":"publisher","first-page":"5521","DOI":"10.1002\/anie.201912613","article-title":"An Unexpected\nTransannular [4 + 2]\nCycloaddition during the Total Synthesis of (+)-Norcembrene 5","volume":"59","author":"Breunig","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"issue":"13","key":"2026101608084859300_cit18","doi-asserted-by":"publisher","first-page":"2566","DOI":"10.1021\/jo01301a003","article-title":"Synthetic Applications\nof Metal Halides. Conversion\nof Cyclopropylmethanols into Homoallylic Halides","volume":"45","author":"McCormick","year":"1980","journal-title":"J. Org. Chem."},{"issue":"9","key":"2026101608084859300_cit19","doi-asserted-by":"publisher","first-page":"1745","DOI":"10.1021\/ja00868a057","article-title":"A New Synthesis\nof 1,1-Dibromoo\u0308lefins\nvia Phosphine-Dibromomethylenes. the Reaction of Triphenylphosphine\nwith Carbon Tetrabromide","volume":"84","author":"Ramirez","year":"1962","journal-title":"J. Am. Chem. Soc."},{"issue":"46","key":"2026101608084859300_cit20","doi-asserted-by":"publisher","first-page":"9817","DOI":"10.1021\/acs.orglett.4c03483","article-title":"Chemoselective Preparation\nof Alkynes from Vicinal and Geminal Dibromoalkenes","volume":"26","author":"Okumura","year":"2024","journal-title":"Org. Lett."},{"issue":"5","key":"2026101608084859300_cit21","doi-asserted-by":"publisher","first-page":"762","DOI":"10.1002\/anie.200503519","article-title":"Widely Applicable\nPd-Catalyzed Trans-Selective Monoalkylation\nof Unactivated 1,1-Dichloro-1-Alkenes and Pd-Catalyzed Second Substitution\nfor the Selective Synthesis of E or Z Trisubstituted Alkenes","volume":"45","author":"Tan","year":"2006","journal-title":"Angew. Chem., Int. Ed."},{"issue":"6","key":"2026101608084859300_cit22","doi-asserted-by":"publisher","first-page":"2220","DOI":"10.1021\/jo061908w","article-title":"Suzuki\u2013Miyaura\nCross-Coupling of 1,1-Dichloro-1-Alkenes with 9-Alkyl-9-BBN","volume":"72","author":"Liron","year":"2007","journal-title":"J. Org. Chem."},{"issue":"7","key":"2026101608084859300_cit23","doi-asserted-by":"publisher","first-page":"1237","DOI":"10.1016\/j.tetlet.2006.12.044","article-title":"Preparation\nof 2-Trimethylsilylmethyl-1-Alkene;\nCross-Coupling and Protodesilylation Sequence from 1,1-Dibromo-1-Alkene","volume":"48","author":"Uenishi","year":"2007","journal-title":"Tetrahedron Lett."},{"issue":"4","key":"2026101608084859300_cit24","doi-asserted-by":"publisher","first-page":"423","DOI":"10.1021\/ol0272693","article-title":"Highly Efficient,\nGeneral Procedure for the Preparation of Alkylzinc Reagents from Unactivated\nAlkyl Bromides and Chlorides","volume":"5","author":"Huo","year":"2003","journal-title":"Org. Lett."},{"issue":"36","key":"2026101608084859300_cit25","doi-asserted-by":"publisher","first-page":"8654","DOI":"10.1021\/ja0015287","article-title":"Evolution\nof a Gram-Scale Synthesis of (+)-Discodermolide","volume":"122","author":"Smith","year":"2000","journal-title":"J. Am. Chem. Soc."},{"issue":"3","key":"2026101608084859300_cit26","doi-asserted-by":"publisher","first-page":"357","DOI":"10.1016\/j.tetlet.2015.12.022","article-title":"Towards the Total Synthesis\nof the Anti-Trypanosomal Macrolide, Actinoallolides: Construction\nof a Key Linear Intermediate","volume":"57","author":"Oshita","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"2026101608084859300_cit27","doi-asserted-by":"publisher","DOI":"10.1002\/047084289X.rl090.pub2","article-title":"Lithium Dibutylcuprate","author":"Dieter","year":"2007","journal-title":"Encyclopedia\nof Reagents for Organic Synthesis"},{"issue":"6","key":"2026101608084859300_cit28","doi-asserted-by":"publisher","first-page":"861","DOI":"10.1016\/j.tetlet.2005.12.002","article-title":"Synthesis\nof Alicyclic Esters via an Intramolecular Conjugate Addition Reaction.\nNew Method for Generating (Z)-Vinylcopper Species from 1,1-Dibromoalkenes","volume":"47","author":"Tanino","year":"2006","journal-title":"Tetrahedron Lett."},{"issue":"5","key":"2026101608084859300_cit29","doi-asserted-by":"publisher","first-page":"539","DOI":"10.1016\/S0040-4039(00)95247-X","article-title":"Rhodium\nComplexes of Trisubstituted Olefins: Syn Selective Directed Hydrocarboxylation","volume":"30","author":"Krafft","year":"1989","journal-title":"Tetrahedron Lett."},{"issue":"13","key":"2026101608084859300_cit30","doi-asserted-by":"publisher","first-page":"3540","DOI":"10.1021\/acs.orglett.7b01513","article-title":"Synthesis of (\u2212)-6,7-Dideoxysqualestatin\nH5\nby Carbonyl Ylide Cycloaddition-Rearrangement and Cross-Electrophile\nCoupling","volume":"19","author":"Fegheh-Hassanpour","year":"2017","journal-title":"Org. Lett."},{"issue":"11","key":"2026101608084859300_cit31","doi-asserted-by":"publisher","first-page":"4793","DOI":"10.1021\/jo500507s","article-title":"Cross-Electrophile\nCoupling: Principles of Reactivity\nand Selectivity","volume":"79","author":"Everson","year":"2014","journal-title":"J. Org. Chem."},{"issue":"14","key":"2026101608084859300_cit32","doi-asserted-by":"publisher","first-page":"6146","DOI":"10.1021\/ja301769r","article-title":"Replacing Conventional Carbon Nucleophiles\nwith Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl\nBromides and Chlorides","volume":"134","author":"Everson","year":"2012","journal-title":"J. Am. Chem. Soc."},{"issue":"20","key":"2026101608084859300_cit33","doi-asserted-by":"publisher","first-page":"3596","DOI":"10.1021\/acs.orglett.3c00635","article-title":"Synthesis of a Halicyclamine-Type\nMacrocyclic Scaffold via Biomimetic\nTransannular Cyclization","volume":"25","author":"Wayama","year":"2023","journal-title":"Org. Lett."},{"issue":"22","key":"2026101608084859300_cit34","doi-asserted-by":"publisher","first-page":"6601","DOI":"10.1002\/chem.200500417","article-title":"Enantioselective Total Synthesis\nof Octalactin a Using Asymmetric Aldol Reactions and a Rapid Lactonization\nto Form a Medium-Sized Ring","volume":"11","author":"Shiina","year":"2005","journal-title":"Chem.\u2500Eur.\nJ."},{"issue":"12","key":"2026101608084859300_cit35","doi-asserted-by":"publisher","first-page":"2998","DOI":"10.1021\/ol401186f","article-title":"Synthesis of Eukaryotic Translation Elongation Inhibitor\nLactimidomycin via Zn(II)-Mediated Horner\u2013Wadsworth\u2013Emmons\nMacrocyclization","volume":"15","author":"Larsen","year":"2013","journal-title":"Org. Lett."},{"issue":"21","key":"2026101608084859300_cit36","doi-asserted-by":"publisher","first-page":"3654","DOI":"10.1055\/s-2006-950292","article-title":"Mild Zinc-Promoted\nHorner-Wadsworth-Emmons Reactions\nof Diprotic Phosphonate Reagents","volume":"2006","author":"Schauer","year":"2006","journal-title":"Synthesis\n(Stuttg)."},{"issue":"49","key":"2026101608084859300_cit37","doi-asserted-by":"publisher","first-page":"17160","DOI":"10.1021\/ja052939w","article-title":"Prevention of Undesirable\nIsomerization during Olefin Metathesis","volume":"127","author":"Hong","year":"2005","journal-title":"J. Am.\nChem. Soc."},{"issue":"9","key":"2026101608084859300_cit38","doi-asserted-by":"publisher","first-page":"2948","DOI":"10.1021\/jo9721195","article-title":"Highly Regio-\nand Enantioselective Monoepoxidation of Conjugated Dienes","volume":"63","author":"Frohn","year":"1998","journal-title":"J. Org. Chem."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01838","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/doi\/10.1021\/acs.joc.6c01838\/68709854\/acs.joc.6c01838.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/doi\/10.1021\/acs.joc.6c01838\/68709854\/acs.joc.6c01838.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T12:23:22Z","timestamp":1792153402000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/41\/13793\/5442267\/The-Convergent-Synthetic-Efforts-toward-Knightol"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,30]]},"references-count":38,"journal-issue":{"issue":"41","published-online":{"date-parts":[[2026,9,30]]},"published-print":{"date-parts":[[2026,10,16]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01838","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,30]]}}}