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Stereoselective Total Synthsis of (±)-Urechitol A

Authors

  • Tatsunobu Sumiya,

    1. Research fellow from Discovery Research Laboratories, Kyorin Pharmaceutical Co., Ltd., 2399-1 Nogi, Nogi-Machi, Shimotsuga-gun, Tochigi 329-0114 (Japan)
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  • Ken Ishigami Dr.,

    1. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bukyo-ku, Tokyo 113-8657 (Japan), Fax: (+81) 3-5841-8019
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  • Hidenori Watanabe Prof. Dr.

    1. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bukyo-ku, Tokyo 113-8657 (Japan), Fax: (+81) 3-5841-8019
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  • We are grateful to Dr. L. M. Peña-Rodríguez for providing NMR spectra of natural urechitol A.

Abstract

original image

Der zentrale Tricyclus von Urechitol A wurde mithilfe einer [4+3]-Cycloaddition und einer methanolvermittelten intramolekularen Epoxidöffnung als Schlüsselschritte effizient aufgebaut. Die Gesamtausbeute an racemischem Produkt über 12 Stufen betrug 2.3 %.

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