Stereoselective total synthesis of marine cyclodepsipeptide calcaripeptides A-C

Article abstract of DOI:10.1021/jo5019798

The first stereoselective total syntheses of marine cyclodepsipeptides, calcaripeptides A-C, have been accomplished. Emphasis was given particularly in identification of an efficient strategy for the macrocyclization. The notable features of our synthesis include Evans alkylation, Crimmins syn-aldol, Crimmins acetate aldol, Wittig olefination, and Shiina macrolactonization reactions. An anomaly in the ¹H NMR of the proposed calcaripeptide B has been amended during this synthetic study. (Chemical Equation Presented).