2026-04-17T03:14:30Zhttps://recercat.cat/oai/request

oai:recercat.cat:2445/1548282025-12-04T21:41:49Zcom_2072_1057col_2072_478917col_2072_478933

00925njm 22002777a 4500 dc Bosch Hereu, Lluís author Mola Solà, Laura author Petit Roig, Elena author Saladrigas, Mar author Esteban Jarne, Jordi author Costa i Arnau, Anna M. author Vilarrasa i Llorens, Jaume author 2020-04-02T09:43:13Z 2020-04-02T09:43:13Z 2017-10-20 2020-04-02T09:43:13Z 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. Síntesi orgànica Enllaços químics Organic synthesis Chemical bonds Formal total synthesis of amphidinolide E