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A Concise Total Synthesis of ( R )‐Puraquinonic Acid
Author(s) -
Tiong Erica A.,
Rivalti Daniel,
Williams Benjamin M.,
Gleason James L.
Publication year - 2013
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.201208792
Subject(s) - stereocenter , total synthesis , bicyclic molecule , natural product , stereochemistry , quaternary , combinatorics , mathematics , chemistry , biology , organic chemistry , paleontology , enantioselective synthesis , catalysis
Distant relative: The configuration of the quaternary stereocenter in puraquinonic acid (see scheme, right) is defined by groups far removed from the point of asymmetry. The use of a bicyclic thioglycolate lactam to set the quaternary stereocenter at an early stage cuts the length of the synthesis of the natural product by nearly two thirds.