Asymmetric Total Synthesis of (+)‐Mannolide C | Zendy

Ao Qiaoqiao | Zendy; Zhang HaiJun | Zendy; Zheng Jinbin | Zendy; Chen Xiaoming | Zendy; Zhai Hongbin | Zendy

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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

Abstract (+)‐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.

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