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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:
It is part of: Journal of Organic Chemistry, 2017, vol. 82, num. 20, p. 11021-11034
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ISSN: 0022-3263
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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