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Total Synthesis of (−)‐Glaucocalyxin A
Author(s) -
Guo Jiuzhou,
Li Bo,
Ma Weihao,
Pitchakuntla Mallesham,
Jia Yanxing
Publication year - 2020
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.202005932
Subject(s) - total synthesis , conjugate , chemistry , enantioselective synthesis , aldol reaction , ring (chemistry) , acylation , intramolecular force , octane , stereochemistry , aldol condensation , bicyclic molecule , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , mathematics
A practically useful method for the formation of the highly oxygenated bicyclo[3.2.1]octane ring system through Mn(OAc) 3 ‐mediated radical cyclization of alkynyl ketones was developed, which opens up a new avenue for the total synthesis of a number of highly oxidized diterpenoids. Application of this method enabled the first total synthesis of (−)‐glaucocalyxin A. Other salient features of the synthesis include a highly enantioselective conjugate addition/acylation cascade reaction, a Yamamoto aldol reaction, and an intramolecular Diels–Alder reaction to assemble the A/B ring system.
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