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An Efficient Stereoselective Total Synthesis of dl ‐Sesquicillin, a Glucocorticoid Antagonist
Author(s) -
Zhang Fei,
Danishefsky Samuel J.
Publication year - 2002
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 - 10.1002/1521-3773(20020415)41:8<1434::aid-anie1434>3.0.co;2-a
Subject(s) - stereoselectivity , moiety , total synthesis , chemistry , stereochemistry , claisen rearrangement , sequence (biology) , antagonist , combinatorial chemistry , organic chemistry , biochemistry , catalysis , receptor
The key step in the total synthesis of sesquicillin ( 3 ) is a stereoselective Claisen rearrangement of 1 to afford 2 . The synthesis also features an efficient sequence to install an α ‐pyrone moiety in a hindered environment; TBS = tert ‐butyldimethylsilyl.