An Enantioconvergent and Concise Synthesis of Lasonolide A

作者：Lin Yang, Zuming Lin, Shunjie Shao, Qian Zhao, Ran Hong · 发表于：Angewandte Chemie International Edition · 年份：2018 · DOI：10.1002/anie.201811093 · 被引用次数：30 · 研究领域：Synthetic Organic Chemistry Methods、Marine Sponges and Natural Products、Synthesis and Biological Activity

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.