Stereoselective Total Synthesis of (+)-Norrisolide

Authors

  • Thomas P. Brady,

    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, MC, 0358 La Jolla, CA 92093-0358, USA, Fax: (+1) 858-822-0386
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  • Sun Hee Kim,

    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, MC, 0358 La Jolla, CA 92093-0358, USA, Fax: (+1) 858-822-0386
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  • Ke Wen,

    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, MC, 0358 La Jolla, CA 92093-0358, USA, Fax: (+1) 858-822-0386
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  • Emmanuel A. Theodorakis Prof.

    1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, MC, 0358 La Jolla, CA 92093-0358, USA, Fax: (+1) 858-822-0386
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  • Financial support from the NIH (CA 086079) is gratefully acknowledged. We also thank Dr. L. N. Zakharov and Dr. P. Gantzel (UCSD, X-Ray Facility) for the crystallographic studies reported and Professor D. J. Faulkner (Scripps Institute of Oceanography) for a sample of natural norrisolide.

Abstract

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In a convergent approach to the marine natural product (+)-norrisolide (1) the two bicyclic ring systems are coupled through the C9[BOND]C10 bond to assemble the carbon framework in a late stage of the synthesis. Other highlights of the synthetic strategy include the formation of the unusual fused γ-lactone–γ-lactol motif of 1 through a sequence of oxidation reactions.

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