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    A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D

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    Type
    Article
    Authors
    Nelson, Hosea M.
    Murakami, Kei
    Virgil, Scott C.
    Stoltz, Brian M.
    KAUST Grant Number
    KUS-11-006-02
    Date
    2011-03-25
    Online Publication Date
    2011-03-25
    Print Publication Date
    2011-04-11
    Permanent link to this record
    http://hdl.handle.net/10754/597275
    
    Metadata
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    Abstract
    (Figure Presented) In a flash: The total synthesis of transtaganolide and basiliolide natural products is achieved in three steps from achiral, monocyclic esters (see scheme). Featured in the syntheses are an Ireland-Claisen/Diels- Alder cascade and a novel methoxyacetylide coupling/cyclization sequence. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.
    Citation
    Nelson HM, Murakami K, Virgil SC, Stoltz BM (2011) A General Approach to the Basiliolide/Transtaganolide Natural Products: Total Syntheses of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D. Angew Chem Int Ed 50: 3688–3691. Available: http://dx.doi.org/10.1002/anie.201008003.
    Sponsors
    This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank the NSF and Ford Foundation (predoctoral fellowship to H.M.N.), the Japan Society for the Promotion of Science (fellowship for K. M.), Amgen, Abbott, Boehringer Ingelheim, the Gordon and Betty Moore Foundation, and Caltech for financial support. Dr. J. T. Mohr is gratefully acknowledged for useful discussions. Larry Henling and Dr. Michael Day are acknowledged for X-ray analysis of 1a. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech, CHE-0639094.
    Publisher
    Wiley
    Journal
    Angewandte Chemie
    DOI
    10.1002/anie.201008003
    PubMed ID
    21442697
    ae974a485f413a2113503eed53cd6c53
    10.1002/anie.201008003
    Scopus Count
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    Publications Acknowledging KAUST Support

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