Please use this identifier to cite or link to this item:
http://hdl.handle.net/2445/154828
Title: | Formal total synthesis of amphidinolide E |
Author: | Bosch Hereu, Lluís Mola Solà, Laura Petit, Elena Saladrigas, Mar Esteban, Jorge Costa i Arnau, Anna M. Vilarrasa i Llorens, Jaume |
Keywords: | Síntesi orgànica Enllaços químics Organic synthesis Chemical bonds |
Issue Date: | 20-Oct-2017 |
Publisher: | American Chemical Society |
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. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.7b01973 |
It is part of: | Journal of Organic Chemistry, 2017, vol. 82, num. 20, p. 11021-11034 |
URI: | http://hdl.handle.net/2445/154828 |
Related resource: | https://doi.org/10.1021/acs.joc.7b01973 |
ISSN: | 0022-3263 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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