Total Synthesis of the Marine Macrolide Amphidinolide
F
Laurent Ferrié
Johan Fenneteau
Bruno Figadère
10.1021/acs.orglett.8b01020.s001
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_the_Marine_Macrolide_Amphidinolide_F/6270287
A new and efficient
convergent approach toward the synthesis of
amphidinolide F is described through the assembly of three fragments.
The two <i>trans</i>-tetrahydrofurans were built by a diastereoselective <i>C</i>-glycosylation with titanium enolate of bulky <i>N</i>-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.
2018-05-15 15:33:59
tran
sequence
side chain
macrolactonization
glycosylation
sulfone
convergent approach
tetrahydrofuran
acetyloxazolidinethione
Liebeskind
synthesis
assembly
fragment
Total Synthesis
condensation
diastereoselective C
Marine Macrolide Amphidinolide F
amphidinolide F
Stille cross-coupling
titanium enolate