A Unified Approach for the Enantioselective Synthesis of the Brominated Chamigrene Sesquiterpenes.

ABSTRACT: 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.

SUBMITTER: Burckle AJ 

PROVIDER: S-EPMC5505624 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature