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Formal total synthesis of amphidinolide E

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dc.contributor.authorBosch Hereu, Lluís
dc.contributor.authorMola Solà, Laura
dc.contributor.authorPetit Roig, Elena
dc.contributor.authorSaladrigas, Mar
dc.contributor.authorEsteban Jarne, Jordi
dc.contributor.authorCosta i Arnau, Anna M.
dc.contributor.authorVilarrasa i Llorens, Jaume
dc.date.accessioned2020-04-02T09:43:13Z
dc.date.available2020-04-02T09:43:13Z
dc.date.issued2017-10-20
dc.date.updated2020-04-02T09:43:13Z
dc.description.abstractA formal total synthesis of the cytotoxic macrolide amphidinolide E is reported. The strategic steps are three Julia-Kocienski reactions (J-K), for the formation of the C5-C6, C9-C10, and C17-C18 double bonds, a Suzuki-Molander C21-C22 bond formation reaction, and a Kita-Trost macrolactonization. The 'instability' of the two dienic systems and of the stereocenter at C2 (allylic methine, alpha to the carboxy group) and the protecting groups at C17-OH and C18-OH have posed difficult challenges. Each Julia-Kocienski olefination has been systematically optimized to provide the highest possible E/Z ratios.
dc.format.extent14 p.
dc.format.mimetypeapplication/pdf
dc.identifier.idgrec677636
dc.identifier.issn0022-3263
dc.identifier.urihttps://hdl.handle.net/2445/154828
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.isformatofVersió postprint del document publicat a: https://doi.org/10.1021/acs.joc.7b01973
dc.relation.ispartofJournal of Organic Chemistry, 2017, vol. 82, num. 20, p. 11021-11034
dc.relation.urihttps://doi.org/10.1021/acs.joc.7b01973
dc.rights(c) American Chemical Society , 2017
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.sourceArticles publicats en revistes (Química Inorgànica i Orgànica)
dc.subject.classificationSíntesi orgànica
dc.subject.classificationEnllaços químics
dc.subject.otherOrganic synthesis
dc.subject.otherChemical bonds
dc.titleFormal total synthesis of amphidinolide E
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/acceptedVersion

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