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Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin

Authors

  • Yasuhito Koyama 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
    2. Present address: Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
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  • Ryo Yamaguchi,

    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 are grateful to Dr. Hidehiro Uekusa for X-ray analyses. This work was partially supported by the Global COE program (Tokyo Institute of Technology) and a Grant-in-Aid for Scientific Research (JSPS). A Fellowship to Y.K. from the JSPS for Young Japanese Scientists is gratefully acknowledged. We thank Dr. Liselotte Krenn (Vienna University) for providing an authentic sample of cassialoin and the 1H NMR spectrum.

Abstract

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Konfiguration komplett: Die erste Totalsynthese und die Strukturbestimmung des Anthron-C-Glycosids Cassialoin (1) gelangen mithilfe eines stereogenen α-Ketols mit Isoxazolring, das eine intramolekulare Redoxreaktion einging (siehe die Retrosynthese; MOM = Methoxymethyl).

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