Total Synthesis as a Resource in the Discovery of Potentially Valuable Antitumor Agents: Cycloproparadicicol

Authors

  • Kana Yamamoto Dr.,

    1. 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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  • Robert M. Garbaccio Dr.,

    1. Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
    2. Current address:, Merck Research Laboratories, West Point, PA 19486, USA
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  • Shawn J. Stachel Dr.,

    1. Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
    2. Current address:, Merck Research Laboratories, West Point, PA 19486, USA
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  • David B. Solit Dr.,

    1. Program in Cell Biology and Department of Medicine, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA
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  • Gabriela Chiosis Dr.,

    1. Program in Cell Biology and Department of Medicine, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA
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  • Neal Rosen Prof.,

    1. Program in Cell Biology and Department of Medicine, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA
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  • Samuel J. Danishefsky Prof. Dr.

    1. Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
    2. Department of Chemistry, Columbia University, Havemeyer Hall, New York, NY 10027, USA
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  • Support for this research was provided by the National Institutes of Health (CA28824). Postdoctoral Fellowship support is gratefully acknowledged by K.Y. (The Helen Hay Whitney Foundation), R.M.G. (NIH, 1 F32 CA85894-01), and S.J.S. (NIH, 1 F32 CA81704). Dr. George Sukenick (NMR Core Facility, Sloan-Kettering Institute) is acknowledged for NMR and mass spectrometric analyses. We thank Dr. Louis J. Todaro (The CUNY X-ray Facility, Hunter College) and Dr. David G. Churchill (Department of Chemistry, Columbia University) for X-ray analyses.

Abstract

original image

Durch eine hoch konvergente Synthese gelang die Herstellung einer Reihe von Epimeren und Analoga von Radicicol (1). Biologische Tests offenbarten eine bis dahin nicht bekannte Korrelation zwischen der Stereochemie und dem Potenzial dieser Verbindungen als Tumortherapeutika. So zeigt Cycloproparadicicol (2) vielversprechende therapeutische Eigenschaften, die auf ihrer Chaperon-inhibierenden Wirkung beruhen.

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