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A Three‐Step Entry to the Aspirochlorine Family of Antifungal Agents
Author(s) -
Wu Zhicai,
Williams Lawrence J.,
Danishefsky Samuel J.
Publication year - 2000
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(20001103)39:21<3866::aid-anie3866>3.0.co;2-e
Subject(s) - antifungal , piperazine , sulfur , ring (chemistry) , yield (engineering) , chemistry , stereochemistry , stereoselectivity , combinatorial chemistry , biology , biochemistry , organic chemistry , microbiology and biotechnology , materials science , metallurgy , catalysis
The quest for superior antifungal agents will be aided by the unprecedented sulfur migration of an epidithioketopiperazine (EDKP) in a highly stereoselective manner and in high yield. The rearrangement provides a short route to compounds in the same family as aspirochlorine ( 1 ), a potent inhibitor of fungal protein synthesis. In this family one of the dithio sulfur atoms is anchored to a dihydrobenzofuran ring that is spiro fused to the piperazine ring.