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    A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B

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    Type
    Article
    Authors
    Mukherjee, Herschel
    McDougal, Nolan T.
    Virgil, Scott C.
    Stoltz, Brian M.
    KAUST Grant Number
    K US-11-006-02
    Date
    2011-03-04
    Permanent link to this record
    http://hdl.handle.net/10754/597227
    
    Metadata
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    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.
    Citation
    Mukherjee H, McDougal NT, Virgil SC, Stoltz BM (2011) A Catalytic, Asymmetric Formal Synthesis of (+)-Hamigeran B. Organic Letters 13: 825–827. Available: http://dx.doi.org/10.1021/ol102669z.
    Sponsors
    This publication is based on work supported by Award No. K US-11-006-02, made by King Abdullah University of Science and Technology (KAUST). Additionally, the authors wish to thank NIH-NIGMS (R01 GM 080269-01), Abbott Laboratories, Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support and Materia, Inc. for the kind donation of catalyst 8. Dr. Douglas C. Behenna is gratefully acknowledged for assistance in the preparation of the manuscript.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organic Letters
    DOI
    10.1021/ol102669z
    PubMed ID
    21271716
    PubMed Central ID
    PMC3045637
    ae974a485f413a2113503eed53cd6c53
    10.1021/ol102669z
    Scopus Count
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