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First Desymmetrization of a Centrosymmetric Molecule in Natural Product Synthesis: Preparation of a Key Fragment in the Synthesis of Hemibrevetoxin B
Author(s) -
Holland Joanne M.,
Lewis Mark,
Nelson Adam
Publication year - 2001
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(20011105)40:21<4082::aid-anie4082>3.0.co;2-t
Subject(s) - desymmetrization , enantioselective synthesis , total synthesis , fragment (logic) , chemistry , stereochemistry , molecule , epoxide , hydrolysis , combinatorial chemistry , organic chemistry , catalysis , computer science , programming language
Exploitation of molecular symmetry can greatly improve the efficiency of syntheses. The symmetry embedded in the centrosymmetric AB dioxepane fragment of hemibrevetoxin B was exploited for the first time in the preparation of an established intermediate in its total synthesis. Desymmetrization of the centrosymmetric diepoxide 1 by enantioselective epoxide hydrolysis followed by acetonization gave the known synthetic intermediate 2 .