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Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-anverene.

ABSTRACT: The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (-)-anverene.

SUBMITTER: Seidl FJ

PROVIDER: S-EPMC4979643 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-anverene.

Seidl Frederick J FJ Burns Noah Z NZ

Beilstein journal of organic chemistry 20160701

The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (-)-anverene. ...[more]

PMID: 27559385

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