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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202107954
Subject(s) - stereocenter , allylic rearrangement , total synthesis , stereochemistry , chemistry , enantioselective synthesis , metathesis , salt metathesis reaction , catalysis , kinetic resolution , ring closing metathesis , 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.