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Enantioselective synthesis of (-)-sclerophytin A by a stereoconvergent epoxide hydrolysis.


ABSTRACT: The cytotoxic natural product (-)-sclerophytin A was constructed in 13 steps from geranial. Highlights from the synthesis are a stereoselective Oshima-Utimoto reaction, a Shibata-Baba indium-promoted radical cyclization, and a novel stereoconvergent epoxide hydrolysis.

SUBMITTER: Wang B 

PROVIDER: S-EPMC3005712 | biostudies-other | 2010 Nov

REPOSITORIES: biostudies-other

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Enantioselective synthesis of (-)-sclerophytin A by a stereoconvergent epoxide hydrolysis.

Wang Bin B   Ramirez Armando P AP   Slade Justin J JJ   Morken James P JP  

Journal of the American Chemical Society 20101028 46


The cytotoxic natural product (-)-sclerophytin A was constructed in 13 steps from geranial. Highlights from the synthesis are a stereoselective Oshima-Utimoto reaction, a Shibata-Baba indium-promoted radical cyclization, and a novel stereoconvergent epoxide hydrolysis. ...[more]

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