Formal total synthesis of amphidinolide E

Bosch Hereu, LluísMola Solà, LauraPetit Roig, ElenaSaladrigas, MarEsteban Jarne, JordiCosta i Arnau, Anna M.Vilarrasa i Llorens, Jaume2020-04-022020-04-022017-10-200022-3263https://hdl.handle.net/2445/154828A 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.14 p.application/pdfeng(c) American Chemical Society , 2017Síntesi orgànicaEnllaços químicsOrganic synthesisChemical bondsFormal total synthesis of amphidinolide Einfo:eu-repo/semantics/article6776362020-04-02info:eu-repo/semantics/openAccess