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Total Synthesis of Peribysin E Necessitates Revision of the Assignment of its Absolute Configuration
Author(s) -
Angeles Angie R.,
Dorn David C.,
Kou Cynthia A.,
Moore Malcolm A. S.,
Danishefsky Samuel J.
Publication year - 2007
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.200604308
Subject(s) - absolute configuration , computer science , stereochemistry , enantiomer , chemistry , content (measure theory) , mathematics , mathematical analysis
The right way round : Peribysin E, a naturally occurring adhesion inhibitor, has been synthesized and, as a result, its absolute configuration reassigned. The natural and nonnatural enantiomers can be reached starting from ( R )‐ or ( S )‐carvone, respectively. A key step is the ring contraction of 1 to 2 (see scheme, TBS= tert ‐butyldimethylsilyl, TES=triethylsilyl).