Synthetic study of a moss-produced oxylipin and its structural revision

Hiroki Soeda, Ryo Towada, Yusuke Ogura, Tomoyo Mohri, Georg Pohnert, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    2 Citations (Scopus)

    Abstract

    The proposed structure for a moss-produced acetylenic oxylipin (10-keto-type structure) was synthesized from a known glycidol derivative by an 11-step sequence involving epoxide ring opening with a terminal acetylene and enzymatic hydrolysis of a methyl ester intermediate. The NMR spectra of the proposed structure was, however, different from those of the natural oxylipin, which prompted us to synthesize its 9-epi-isomer and two diastereomeric 12-keto-type positional isomers. Comparison of the NMR spectra of the three isomers with those of the natural oxylipin indicated that the natural oxylipin was actually a mixture of the two diastereomeric positional isomers.

    Original languageEnglish
    Pages (from-to)1555-1562
    Number of pages8
    JournalTetrahedron
    Volume75
    Issue number11
    DOIs
    Publication statusPublished - 2019 Mar 15

    Keywords

    • Antifeedant
    • Dicranum scoparium
    • Oxylipin
    • Structural revision
    • Total synthesis
    • WOKXCSJTLUSNID-HGZAPXNNSA-N
    • WOKXCSJTLUSNID-XADBDUFWSA-N

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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