Total Synthesis of the Marine Macrolide Amphidinolide F

Organic Letters
Laurent FerriéBruno Figadère

Abstract

A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.

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Citations

Aug 29, 2018·Angewandte Chemie·Marc HeinrichAlois Fürstner
Dec 24, 2019·Mini Reviews in Medicinal Chemistry·Yinhui Qin, Shutao Ma

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