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Synthesis of Sominone and Its Derivatives Based on an RCM Strategy: Discovery of A Novel Anti-Alzheimer’s Disease Medicine Candidate “Denosomin”
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    Synthesis of Sominone and Its Derivatives Based on an RCM Strategy: Discovery of A Novel Anti-Alzheimer’s Disease Medicine Candidate “Denosomin”
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    Graduate School of Medicine and Pharmaceutical Sciences and Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan, and Research Alliance & Portfolio Strategy, Taiho Pharmaceutical Co. Ltd., 1-2-4 Utikanda, Chiyoda-ku, Tokyo 101-0047, Japan
    †Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama.
    ‡Institute of Natural Medicine, University of Toyama.
    §Taiho Pharmaceutical Co. Ltd.
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    Organic Letters

    Cite this: Org. Lett. 2009, 11, 17, 3970–3973
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    https://doi.org/10.1021/ol901553w
    Published August 4, 2009
    Copyright © 2009 American Chemical Society

    Abstract

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    Synthesis of sominone was achieved starting from dehydroepiandrosterone on the basis of an RCM strategy for the construction of a δ-lactone side chain. This synthetic protocol was applied for the synthesis of several analogous derivatives including 1-deoxy-24-norsominone (denosomin), which was revealed to exhibit notable bioactivities for new antidementia chemotherapy, exceeding the original natural compound sominone.

    Copyright © 2009 American Chemical Society

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    Experimental procedures and compound characterization data for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Organic Letters

    Cite this: Org. Lett. 2009, 11, 17, 3970–3973
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol901553w
    Published August 4, 2009
    Copyright © 2009 American Chemical Society

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