Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media

Shun Hirasawa, Ken Mukai, Shinnosuke Sakai, Shinnosuke Wakamori, Takahiro Hasegawa, Kazunori Souma, Nobuhiro Kanomata, Narihito Ogawa, Mamoru Aizawa, Makoto Emoto

    Research output: Contribution to journalArticle

    Abstract

    Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (-)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here, we report a nine-step chemical synthesis of an azaspirene analogue with a new finding that the natural (-)-azaspirene skeleton easily racemizes in neutral aqueous media.

    Original languageEnglish
    Pages (from-to)14457-14464
    Number of pages8
    JournalJournal of Organic Chemistry
    Volume83
    Issue number23
    DOIs
    Publication statusPublished - 2018 Dec 7

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    Bioactivity
    Chemical properties
    azaspirene
    Biosynthetic Pathways

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Hirasawa, S., Mukai, K., Sakai, S., Wakamori, S., Hasegawa, T., Souma, K., ... Emoto, M. (2018). Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media. Journal of Organic Chemistry, 83(23), 14457-14464. https://doi.org/10.1021/acs.joc.8b02223

    Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media. / Hirasawa, Shun; Mukai, Ken; Sakai, Shinnosuke; Wakamori, Shinnosuke; Hasegawa, Takahiro; Souma, Kazunori; Kanomata, Nobuhiro; Ogawa, Narihito; Aizawa, Mamoru; Emoto, Makoto.

    In: Journal of Organic Chemistry, Vol. 83, No. 23, 07.12.2018, p. 14457-14464.

    Research output: Contribution to journalArticle

    Hirasawa, S, Mukai, K, Sakai, S, Wakamori, S, Hasegawa, T, Souma, K, Kanomata, N, Ogawa, N, Aizawa, M & Emoto, M 2018, 'Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media', Journal of Organic Chemistry, vol. 83, no. 23, pp. 14457-14464. https://doi.org/10.1021/acs.joc.8b02223
    Hirasawa S, Mukai K, Sakai S, Wakamori S, Hasegawa T, Souma K et al. Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media. Journal of Organic Chemistry. 2018 Dec 7;83(23):14457-14464. https://doi.org/10.1021/acs.joc.8b02223
    Hirasawa, Shun ; Mukai, Ken ; Sakai, Shinnosuke ; Wakamori, Shinnosuke ; Hasegawa, Takahiro ; Souma, Kazunori ; Kanomata, Nobuhiro ; Ogawa, Narihito ; Aizawa, Mamoru ; Emoto, Makoto. / Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 23. pp. 14457-14464.
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    AU - Souma, Kazunori

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