dc.contributor.author
Bosch Hereu, Lluís
dc.contributor.author
Mola Solà, Laura
dc.contributor.author
Petit Roig, Elena
dc.contributor.author
Saladrigas, Mar
dc.contributor.author
Esteban Jarne, Jordi
dc.contributor.author
Costa i Arnau, Anna M.
dc.contributor.author
Vilarrasa i Llorens, Jaume
dc.date.issued
2020-04-02T09:43:13Z
dc.date.issued
2020-04-02T09:43:13Z
dc.date.issued
2017-10-20
dc.date.issued
2020-04-02T09:43:13Z
dc.identifier
https://hdl.handle.net/2445/154828
dc.description.abstract
A 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
application/pdf
dc.publisher
American Chemical Society
dc.relation
Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.7b01973
dc.relation
Journal of Organic Chemistry, 2017, vol. 82, num. 20, p. 11021-11034
dc.relation
https://doi.org/10.1021/acs.joc.7b01973
dc.rights
(c) American Chemical Society , 2017
dc.rights
info:eu-repo/semantics/openAccess
dc.source
Articles publicats en revistes (Química Inorgànica i Orgànica)
dc.subject
Síntesi orgànica
dc.subject
Enllaços químics
dc.subject
Organic synthesis
dc.subject
Chemical bonds
dc.title
Formal total synthesis of amphidinolide E
dc.type
info:eu-repo/semantics/article
dc.type
info:eu-repo/semantics/acceptedVersion
