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An Efficient and Concise Enantioselective Total Synthesis of Lactacystin
Author(s) -
Corey E. J.,
Li Weidong,
Nagamitsu Tohru
Publication year - 1998
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/(sici)1521-3773(19980703)37:12<1676::aid-anie1676>3.0.co;2-t
Subject(s) - lactacystin , enantioselective synthesis , proteasome , total synthesis , isopropyl , chemistry , substituent , proteasome inhibitor , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , catalysis
A selective, irreversible inhibitor of proteasome function , lactacystin ( 1 ) is an important experimental tool in cell biology. An efficient and direct enantioselective synthesis of lactacystin proceeds via the intermediates shown below. This process allows for the first time easy access to analogues of lactacystin in which the isopropyl substituent is replaced by other lipophilic groups. PMB= p ‐methoxybenzyl.