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

2 Citations (Scopus)

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

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    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, 83(23), 14457-14464. https://doi.org/10.1021/acs.joc.8b02223