Total synthesis of (+)-lepadin F.

ABSTRACT: 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.

SUBMITTER: Li G 

PROVIDER: S-EPMC2662136 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature