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Stereoselective Total Synthesis of (−)-Borrelidin

Authors

  • Binh G. Vong,

    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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  • Sunny Abraham,

    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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  • In honor of Professor E. J. Corey, recipient of the 2004 Priestley Medal. 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 reported crystallographic studies and Professor D. B. Ball, California State University, Chico, for a sample of natural borrelidin.

Abstract

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Eine konvergente Synthese von (−)-Borrelidin (1), die auf den im Bild gekennzeichneten retrosynthetischen Spaltungen beruht, enthält als zentrale Elemente den Aufbau eines gespannten, eine Eninon-Einheit enthaltenden Makrolids und das regioselektive Einbringen einer Cyangruppe mithilfe einer neuartigen molybdänkatalysierten Hydrostannylierung des Alkins.

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