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Formal Total Synthesis of Amphidinolide E

2017; American Chemical Society; Volume: 82; Issue: 20 Linguagem: Inglês

10.1021/acs.joc.7b01973

1520-6904

Lluís Bosch, Laura Mola, Elena Petit, Mar Saladrigas, Jorge Martín Esteban, Anna M. Costa, Jaume Vilarrasa,

Marine Toxins and Detection Methods

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.