ol8b01020_si_001.pdf (8.95 MB)
Total Synthesis of the Marine Macrolide Amphidinolide F
journal contribution
posted on 2018-05-15, 15:33 authored by Laurent Ferrié, Johan Fenneteau, Bruno FigadèreA 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.