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Total Synthesis of (+)‐Omphadiol
Author(s) -
Liu Gang,
Romo Daniel
Publication year - 2011
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.201102289
Subject(s) - stereocenter , stereochemistry , total synthesis , chemistry , aldol reaction , cyclopropanation , sesquiterpene , cyclopentane , lactone , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis
A smooth transition from ( R )‐carvone to a β‐lactone and then to (+)‐omphadiol characterizes the first total synthesis of this sesquiterpene, which was achieved in ten steps and 18 % overall yield. All six contiguous stereogenic centers were introduced in a highly diastereoselective manner. Key steps include a nucleophile‐promoted aldol lactonization, a single‐pot, sequential intra‐/intermolecular dialkylation, a tandem olefin isomerization/RCM, and a cyclopropanation with unusual facial selectivity.