10.1021/ol802068q.s001
Gang Li
Gang
Li
Richard P. Hsung
Richard P.
Hsung
Brian W. Slafer
Brian W.
Slafer
Irina K. Sagamanova
Irina K.
Sagamanova
Total Synthesis of (+)-Lepadin F
American Chemical Society
2008
C 2
episulfide
Lepadin
stereoselective hydrogenation
sequence features
enantioselective
annulation
lepadin
Eschenmoser
stereochemistry
synthesis
homologation
8a
vinylogous amide
contraction
aza
Total Synthesis
2008-11-06 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_Lepadin_F/2902699
An enantioselective total synthesis of (+)-lepadin F is described. The synthetic sequence features an intermolecular aza-[3 + 3] annulation, homologation of a vinylogous amide via Eschenmoser’s episulfide contraction, and a highly stereoselective hydrogenation essential for achieving the 1,3-anti relative stereochemistry at C2 and C8a.