Total Synthesis of the Salicylate Enamide Macrolide Oximidine III: Application of Relay Ring-Closing Metathesis

Authors

  • Xiang Wang,

    1. Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-353-6466
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  • Emma Jean Bowman Dr.,

    1. Department of Molecular, Cell and Developmental Biology, Sinsheimer Labs, University of California, Santa Cruz, CA 95064, USA
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  • Barry J. Bowman Prof.,

    1. Department of Molecular, Cell and Developmental Biology, Sinsheimer Labs, University of California, Santa Cruz, CA 95064, USA
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  • John A. Porco Jr. Prof.

    1. Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-353-6466
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  • We thank Prof. Y. Hayakawa (Tokyo University of Science) for kindly providing an authentic sample of oximidine III, Dr. J. Lee (Boston University) for assistance with NMR spectroscopy, and Mr. R. Shen (Boston University) for helpful suggestions. We thank the National Institutes of Health (Grant no. GM-62842) for research support.

Abstract

original image

Der Inhibitor der Vakuolär-Adenosintriphosphatase, Oximidin III, sowie seine Enamid- und Epoxid-Stereoisomere wurden enantioselektiv synthetisiert (siehe Schema). Die Makrocyclisierung eines wohldefinierten Substrats mit zwei unterschiedlich funktionalisierten Alkenpartnern wurde durch eine Staffel-Ringschlussmetathese-Strategie erleichtert.

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