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Asymmetric Total Synthesis of (+)‐Mannolide C
Author(s) -
Ao Qiaoqiao,
Zhang HaiJun,
Zheng Jinbin,
Chen Xiaoming,
Zhai Hongbin
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202107954
Subject(s) - stereocenter , chemistry , total synthesis , stereochemistry , allylic rearrangement , metathesis , enantioselective synthesis , ring closing metathesis , salt metathesis reaction , catalysis , kinetic resolution , organic chemistry , polymer , polymerization
(+)‐Mannolide C is a complex hexacyclic C 20 cephalotane‐type diterpenoid featuring a highly strained 7/6/6/5 tetracyclic core containing eight consecutive stereocenters and two bridging lactones. The first asymmetric total synthesis of (+)‐mannolide C has been accomplished by lipase‐mediated resolution, Ru‐complex‐catalyzed double ring‐closing metathesis (RCM) reactions, Ni II ‐catalyzed diastereoselective Michael addition, and Mn III ‐catalyzed allylic oxidation as the key transformations.