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Enantioselective Total Synthesis of Batzelladine A
Author(s) -
Shimokawa Jun,
Shirai Koji,
Tanatani Aya,
Hashimoto Yuichi,
Nagasawa Kazuo
Publication year - 2004
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.200353200
Subject(s) - enantioselective synthesis , total synthesis , chemistry , guanidine , tricyclic , natural product , enone , protein subunit , stereochemistry , alcohol , biomimetic synthesis , organic chemistry , catalysis , biochemistry , gene
One‐step formation of an enone from a primary alcohol has been effectively applied in the total synthesis of batzelladine A ( 1 ). Successive 1,3‐dipolar cycloadditions with a subsequent cyclization were used to form the tricyclic guanidine subunit of this natural product, which has the strongest inhibitory activity of HIV gp120‐CD4 binding among the batzelladines.