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A Concise Total Synthesis of (−)‐Berkelic Acid
Author(s) -
Cheng HongGang,
Yang Zhenjie,
Chen Ruiming,
Cao Liming,
Tong WenYan,
Wei Qiang,
Wang Qingqing,
Wu Chenggui,
Qu Shuanglin,
Zhou Qianghui
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014660
Subject(s) - stereocenter , total synthesis , chemistry , michael reaction , cascade , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , enantioselective synthesis , chromatography
Reported here is a concise total synthesis of (−)‐berkelic acid in eight linear steps. This synthesis features a Catellani reaction/oxa‐Michael cascade for the construction of the isochroman scaffold, a one‐pot deprotection/spiroacetalization operation for the formation of the tetracyclic core structure, and a late‐stage Ni‐catalyzed reductive coupling for the introduction of the lateral chain. Notably, four stereocenters are established from a single existing chiral center with excellent stereocontrol during the deprotection/spiroacetalization process. Stereocontrol of the intriguing deprotection/spiroacetalization process is supported by DFT calculations.