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Total Synthesis of the Marine Macrolide Amphidinolide F

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journal contribution
posted on 15.05.2018, 15:33 by Laurent Ferrié, Johan Fenneteau, Bruno Figadère
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.