Total Synthesis of the Protein Phosphatase 2A Inhibitor Lactodehydrothyrsiferol

Authors

  • Dane J. Clausen,

    1. Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 (USA), Fax: (+1) 412-624-8611
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  • Dr. Shuangyi Wan,

    1. Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 (USA), Fax: (+1) 412-624-8611
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  • Prof. Dr. Paul E. Floreancig

    Corresponding author
    1. Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 (USA), Fax: (+1) 412-624-8611
    • Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 (USA), Fax: (+1) 412-624-8611
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  • We thank the National Institutes of Health, Institute of General Medicine (GM062924) for generous support of this work. We thank Prof. José Fernández (Universidad de La Laguna) for copies of the spectra for lactodehydrothyrsiferol.

Abstract

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Cascading epoxides: The squalene-derived polyether lactodehydrothyrsiferol (1) has been prepared through a convergent sequence that features an epoxide-opening cascade to construct the tetrahydrofuran and tetrahydropyran subunits. Additional features include a stereodivergent diene diepoxidation, a monodeoxygenation of a triol, and complex fragment couplings through Suzuki and Nozaki–Hiyama–Kishi reactions.

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