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Total Synthesis of (+)-Isomigrastatin

Authors

  • Isaac J. Krauss Dr.,

    1. The Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
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  • Mihirbaran Mandal Dr.,

    1. Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA
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  • Samuel J. Danishefsky Prof.

    1. The Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
    2. The Department of Chemistry, Columbia University, Havemeyer Hall, New York, NY 10027, USA
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  • Support for this work was provided by the National Institutes of Health (5 R01 CA103823) I.J.K. is grateful for an NIH postdoctoral fellowship (5 F32 AI063976). M.M. is grateful for a US Army grant (DAMD 17–03-1-0444). The authors thank Prof. Ben Shen and members of his group for helpful discussions, spectra, and an authentic sample for comparison. We also thank Dr. Luis Todaro, who is supported by the NIH-RCMI (RR-03037), for X-ray crystallographic work.

Abstract

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Naturstoffe mit geringer Stabilität: Die asymmetrische Totalsynthese des hydrolytisch und thermisch labilen Naturstoffs (+)-Isomigrastatin wurde demonstriert. Die thermodynamische Instabilität der 2E-konfigurierten Doppelbindung in diesem 12-gliedrigen Makrolid wurde durch eine Phosphan-katalysierte Isomerisierung zur 2Z-Konfiguration aufgezeigt.

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