A Boron-Based Synthesis of the Natural Product (+)-trans-Dihydrolycoricidine

Authors

  • Dr. Sarah L. Poe,

    1. Department of Chemistry, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-2705
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  • Prof. Dr. James P. Morken

    Corresponding author
    1. Department of Chemistry, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-2705
    • Department of Chemistry, Boston College, Chestnut Hill, MA 02467 (USA), Fax: (+1) 617-552-2705
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  • We are grateful to the NIH (NIGMS GM-59417 and GM-64451) for financial support of this work.

Abstract

original image

Diastereoselective diboration results in the highly selective 1,4-dihydroxylation of chiral cyclohexadienes (see scheme). Together with the catalytic enantioselective conjugate allylboration, the diene diboration facilitates the asymmetric synthesis of the cytotoxic agent (+)-trans-dihydrolycoricidine (1). pin=pinacol.

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