{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T01:17:03Z","timestamp":1792718223420,"version":"4.5.0"},"reference-count":126,"publisher":"Wiley","issue":"41","license":[{"start":{"date-parts":[[2018,9,17]],"date-time":"2018-09-17T00:00:00Z","timestamp":1537142400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100004189","name":"Max-Planck-Gesellschaft","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004189","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,10,8]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The marine macrolide chagosensine is the only natural product known to date that embodies a <jats:italic>Z<\/jats:italic>,<jats:italic>Z<\/jats:italic>\u2010configured chloro\u20101,3\u2010diene unit. This distinguishing substructure was prepared by a sequence of palladium\u2010catalyzed 1,2\u2010distannation of an alkyne precursor, regioselective Stille cross\u2010coupling at the terminus of the resulting bisstannyl alkene with an elaborated alkenyl iodide, followed by chloro\u2010destannation of the remaining internal site. The preparation of the required substrates centered on cobalt\u2010catalyzed oxidative cyclization reactions of hydroxylated olefin precursors, which allowed the 2,5\u2010<jats:italic>trans<\/jats:italic>\u2010disubstituted tetrahydrofuran rings, embedded into each building block, to be formed with excellent selectivity. The highly strained macrolactone could ultimately be closed under forcing Yamaguchi conditions. Comparison of the spectral data of the synthetic sample with those of authentic chagosensine methyl ester confirmed that the structure of this intriguing compound has been mis\u2010assigned by the isolation team.<\/jats:p>","DOI":"10.1002\/anie.201808937","type":"journal-article","created":{"date-parts":[[2018,8,28]],"date-time":"2018-08-28T10:09:41Z","timestamp":1535450981000},"page":"13575-13581","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Total Synthesis of Putative Chagosensine"],"prefix":"10.1002","volume":"57","author":[{"given":"Marc","family":"Heinrich","sequence":"first","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John J.","family":"Murphy","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marina K.","family":"Ilg","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aur\u00e9lien","family":"Letort","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jakub","family":"Flasz","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Petra","family":"Philipps","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0098-3417","authenticated-orcid":false,"given":"Alois","family":"F\u00fcrstner","sequence":"additional","affiliation":[{"name":"Max-Planck-Institut f\u00fcr Kohlenforschung  45470 M\u00fclheim\/Ruhr Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,9,17]]},"reference":[{"key":"e_1_2_2_1_1","volume-title":"Handbook of Anticancer Drugs from Marine Origin","year":"2015"},{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300240"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.20119"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr3004778"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)01291-5"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2005.90"},{"key":"e_1_2_2_7_1","unstructured":"\u00a0"},{"key":"e_1_2_2_8_2","first-page":"653","volume":"59","author":"Mooberry S. L.","year":"1999","journal-title":"Cancer Res."},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802075v"},{"key":"e_1_2_2_10_1","unstructured":"\u00a0"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/np0605844"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.201100006"},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301700"},{"key":"e_1_2_2_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301700"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405790"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja404796n"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01020"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3897(199907)341:5<417::AID-PRAC417>3.0.CO;2-A"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0341804"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0356789"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja051749i"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja8043695"},{"key":"e_1_2_2_23_1","unstructured":"\u00a0"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800554f"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802806z"},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200800585"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200800585"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1588169"},{"key":"e_1_2_2_28_1","first-page":"2779","author":"Guinchard X.","year":"2011","journal-title":"Synlett"},{"key":"e_1_2_2_29_1","unstructured":"Yet other routes based on RCM RCAM or Sonogashira coupling met with failure; details will be reported in a future full paper."},{"key":"e_1_2_2_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.06.026"},{"key":"e_1_2_2_31_1","unstructured":"\u00a0"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)80030-3"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1139\/v2012-041"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.07.013"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302609"},{"key":"e_1_2_2_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201302609"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00089"},{"key":"e_1_2_2_37_1","unstructured":"\u00a0"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00076a081"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/om950672b"},{"key":"e_1_2_2_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00193"},{"key":"e_1_2_2_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol034284e"},{"key":"e_1_2_2_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3cc47173j"},{"key":"e_1_2_2_43_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9902594"},{"key":"e_1_2_2_44_1","unstructured":"The use of hetero-bimetallic reagents of type R3M\u2212B(pin) or R3M1\u2212M2R3(M=Si Sn) was considered but not pursued in detail."},{"key":"e_1_2_2_45_1","unstructured":"\u00a0"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1996.1117"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.03.012"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol4000263"},{"key":"e_1_2_2_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja076498n"},{"key":"e_1_2_2_50_1","unstructured":"\u00a0"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201003349"},{"key":"e_1_2_2_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201003349"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603350"},{"key":"e_1_2_2_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200603350"},{"key":"e_1_2_2_53_1","unstructured":"Details will be reported in a future full paper."},{"key":"e_1_2_2_54_1","unstructured":"\u00a0"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(91)80222-R"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500353"},{"key":"e_1_2_2_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501608"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201501608"},{"key":"e_1_2_2_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b02871"},{"key":"e_1_2_2_59_1","unstructured":"\u00a0"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200500368"},{"key":"e_1_2_2_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200500368"},{"key":"e_1_2_2_61_2","first-page":"1","volume":"50","author":"Farina V.","year":"1997","journal-title":"Org. React."},{"key":"e_1_2_2_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)00575-4"},{"key":"e_1_2_2_63_1","unstructured":"A terminal stannyl group showed gradually higher reactivity in other transformations see:"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(89)80009-2"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(96)06151-7"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(91)80162-Y"},{"key":"e_1_2_2_67_2","first-page":"1577","author":"Carter N. B.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_2_68_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.07.026"},{"key":"e_1_2_2_69_1","unstructured":"\u00a0"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1990.67"},{"key":"e_1_2_2_71_2","doi-asserted-by":"publisher","DOI":"10.1039\/b804588g"},{"key":"e_1_2_2_72_1","unstructured":"\u00a0"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201201331"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol9023375"},{"key":"e_1_2_2_75_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00997a067"},{"key":"e_1_2_2_76_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)85909-2"},{"key":"e_1_2_2_77_1","unstructured":"Attempted short-cuts by organocatalyticanti-aldol reactions were not at all competitive."},{"key":"e_1_2_2_78_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)99640-0"},{"key":"e_1_2_2_79_1","unstructured":"Attempted replacement of HMPA by DMPU or DMSO met with failure."},{"key":"e_1_2_2_80_1","unstructured":"While the oxidation proceeded cleanly the esterification entailed noticeable epimerization (circa 7\u2009%); for the TEMPO\/BAIB protocol see:"},{"key":"e_1_2_2_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo981316g"},{"key":"e_1_2_2_82_2","doi-asserted-by":"publisher","DOI":"10.1039\/B303249N"},{"key":"e_1_2_2_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo980112x"},{"key":"e_1_2_2_84_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201402010"},{"key":"e_1_2_2_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201402010"},{"key":"e_1_2_2_85_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19930002743"},{"key":"e_1_2_2_86_1","unstructured":"The stereochemistry of the newly formed center was confirmed by Mosher ester analysis; see the Supporting Information."},{"key":"e_1_2_2_87_1","unstructured":"\u00a0"},{"key":"e_1_2_2_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr980379w"},{"key":"e_1_2_2_89_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198405561"},{"key":"e_1_2_2_89_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19840960805"},{"key":"e_1_2_2_90_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo034964v"},{"key":"e_1_2_2_91_1","unstructured":"Slow addition led to epimerization and formation of aldol-type side products."},{"key":"e_1_2_2_92_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00448"},{"key":"e_1_2_2_93_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar800148f"},{"key":"e_1_2_2_94_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9007134"},{"key":"e_1_2_2_95_1","unstructured":"For competing alkenyliodide homocoupling see:"},{"key":"e_1_2_2_96_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20021104)8:21<4843::AID-CHEM4843>3.0.CO;2-I"},{"key":"e_1_2_2_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo100089d"},{"key":"e_1_2_2_98_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja9726926"},{"key":"e_1_2_2_99_1","doi-asserted-by":"publisher","DOI":"10.1039\/b805299a"},{"key":"e_1_2_2_100_1","unstructured":"\u00a0"},{"key":"e_1_2_2_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0301402"},{"key":"e_1_2_2_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr300129n"},{"key":"e_1_2_2_103_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1975.1045"},{"key":"e_1_2_2_104_1","unstructured":"\u00a0"},{"key":"e_1_2_2_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906115a"},{"key":"e_1_2_2_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201602125"},{"key":"e_1_2_2_106_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201602125"},{"key":"e_1_2_2_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05094"},{"key":"e_1_2_2_108_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.52.1989"},{"key":"e_1_2_2_109_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00195a007"},{"key":"e_1_2_2_110_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja508846g"},{"key":"e_1_2_2_111_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)97963-3"},{"key":"e_1_2_2_112_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300827"},{"key":"e_1_2_2_113_1","unstructured":"Reviews:"},{"key":"e_1_2_2_114_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200460864"},{"key":"e_1_2_2_114_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200460864"},{"key":"e_1_2_2_115_2","doi-asserted-by":"publisher","DOI":"10.1039\/b809658a"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201808937","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201808937","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,14]],"date-time":"2023-09-14T05:58:47Z","timestamp":1694671127000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201808937"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,9,17]]},"references-count":126,"journal-issue":{"issue":"41","published-print":{"date-parts":[[2018,10,8]]}},"alternative-id":["10.1002\/anie.201808937"],"URL":"https:\/\/doi.org\/10.1002\/anie.201808937","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,9,17]]},"assertion":[{"value":"2018-08-03","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-09-17","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}