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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

Authors

  • Hosea M. Nelson,

    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 101-20, Pasadena, CA 91125 (USA)
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  • Kei Murakami,

    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 101-20, Pasadena, CA 91125 (USA)
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  • Dr. Scott C. Virgil,

    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 101-20, Pasadena, CA 91125 (USA)
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  • Prof. Dr. Brian M. Stoltz

    Corresponding author
    1. Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 101-20, Pasadena, CA 91125 (USA)
    • Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, Caltech Center for Catalysis and Chemical Synthesis, California Institute of Technology, 1200 E. California Boulevard, MC 101-20, Pasadena, CA 91125 (USA)
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  • 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 1 a. The Bruker KAPPA APEXII X-ray diffractometer used in this study was purchased through an NSF CRIF:MU award to Caltech, CHE-0639094.

Abstract

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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.

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