An Enantioconvergent and Concise Synthesis of Lasonolide A

Efficient access to medicinally significant natural products is an essential basis for the development of pharmaceuticals. The limited availability of marine natural products impedes broad biological evaluation. Despite several elegant syntheses of (−)‐lasonolide A having been reported, a practical synthesis of this potent anticancer polyketide remains elusive. Based on the application of borane as a traceless protecting group and the development of an unprecedented bissulfone reagent for Julia olefination, (−)‐lasonolide A was assembled in an enantioconvergent manner through the application of stereoselective hydroboration, allylation, and oxidation. This concise route may provide a realistic solution for accessing derivatives and analogues. To protect and serve: Stemming from classical hydroboration chemistry, a novel traceless protection strategy for alcohol was designed and implemented in a concise and modular synthesis of the potent antitumor marine polyketide lasonolide A. The given strategy paves the way to readily access derivatives for future medicinal investigation.