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A Unified Approach for the Enantioselective Synthesis of the Brominated Chamigrene Sesquiterpenes
Author(s) -
Burckle Alexander J.,
Vasilev Vasil H.,
Burns Noah Z.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605722
Subject(s) - enantioselective synthesis , solvolysis , chemistry , vicinal , stereospecificity , stereochemistry , stereoisomerism , molecule , combinatorial chemistry , organic chemistry , catalysis , hydrolysis
The brominated chamigrene sesquiterpenes constitute a large subclass of bromocyclohexane‐containing natural products, yet no general enantioselective strategy for the synthesis of these small molecules exists. Herein we report a general strategy for accessing this family of secondary metabolites, including the enantioselective synthesis of (−)‐α‐ and (−)‐ ent ‐β‐bromochamigrene, (−)‐dactylone, and (+)‐aplydactone. Access to these molecules is enabled by a stereospecific bromopolyene cyclization initiated by the solvolysis of an enantiomerically enriched vicinal bromochloride.