Work

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

Year: 2016

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201605722

Authors: Alexander J. Burckle, Vasil H. Vasilev, Noah Z. Burns

Institution: Stanford University

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences

Awards: Selective Halogenation Reactions for the Synthesis of Chiral Bioactive Small Molecules, G883322004