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An Enantioconvergent and Concise Synthesis of Lasonolide A
Author(s) -
Yang Lin,
Lin Zuming,
Shao Shunjie,
Zhao Qian,
Hong Ran
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811093
Subject(s) - hydroboration , polyketide , chemistry , borane , stereoselectivity , combinatorial chemistry , total synthesis , reagent , organic chemistry , catalysis , biosynthesis , enzyme
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.