Formal Total Synthesis of Amphidinolide E
journal contributionposted on 28.09.2017 by Lluís Bosch, Laura Mola, Elena Petit, Mar Saladrigas, Jorge Esteban, Anna M. Costa, Jaume Vilarrasa
Any type of content formally published in an academic journal, usually following a peer-review process.
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, α 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.