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A catalytic, asymmetric formal synthesis of (+)-hamigeran B.

ABSTRACT: A concise asymmetric, formal synthesis of (+)-hamigeran B is reported. A Pd-catalyzed, decarboxylative allylic alkylation, employing a trifluoromethylated derivative of t-BuPHOX, is utilized as the enantioselective step to form the critical quaternary carbon center in excellent yield and enantioselectivity. The product is converted in three steps to a late-stage intermediate previously used in the synthesis of hamigeran B.

SUBMITTER: Mukherjee H

PROVIDER: S-EPMC3045637 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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A catalytic, asymmetric formal synthesis of (+)-hamigeran B.

Mukherjee Herschel H McDougal Nolan T NT Virgil Scott C SC Stoltz Brian M BM

Organic letters 20110127 5

A concise asymmetric, formal synthesis of (+)-hamigeran B is reported. A Pd-catalyzed, decarboxylative allylic alkylation, employing a trifluoromethylated derivative of t-BuPHOX, is utilized as the enantioselective step to form the critical quaternary carbon center in excellent yield and enantioselectivity. The product is converted in three steps to a late-stage intermediate previously used in the synthesis of hamigeran B. ...[more]

PMID: 21271716

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