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.