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Synthesis of (+)-coronafacic acid.

ABSTRACT: An enantioselective synthesis of (+)-coronafacic acid has been achieved. Rhodium-catalyzed cyclization of an alpha-diazoester provided the intermediate cyclopentanone in high enantiomeric purity. Subsequent Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydrogenated and carried on to the natural product.

SUBMITTER: Taber DF

PROVIDER: S-EPMC2662389 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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Synthesis of (+)-coronafacic acid.

Taber Douglass F DF Sheth Ritesh B RB Tian Weiwei W

The Journal of organic chemistry 20090301 6

An enantioselective synthesis of (+)-coronafacic acid has been achieved. Rhodium-catalyzed cyclization of an alpha-diazoester provided the intermediate cyclopentanone in high enantiomeric purity. Subsequent Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydrogenated and carried on to the natural product. ...[more]

PMID: 19231870

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