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Regio- and Stereocontrolled Total Synthesis of Benanomicin B

Authors

  • Ken Ohmori Dr.,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Minoru Tamiya,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Mitsuru Kitamura Dr.,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Hirohisa Kato Dr.,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Mami Oorui,

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • Keisuke Suzuki Prof. Dr.

    1. Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan, Fax: (+81) 3-5734-2788
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  • We thank Meiji Seika Kaisha Ltd. for providing an authentic sample of benanomicins A and B. This work was partially supported by the 21st Century COE program (Tokyo Institute of Technology).

Abstract

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Vollständig kontrolliert gelang die Totalsynthese von Benanomicin B mithilfe zweier Schlüsselschritte: der stereokontrollierten Ringöffnung eines Lactons (Schritt A im Schema) und der Semipinacolcyclisierung eines Acetal-Aldehyd-Derivats, die zur Unterscheidung der beiden OH-Gruppen der pseudo-C2-symmetrischen 1,2-Dioleinheit führt (Schritt B).

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