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

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

    研究成果: Article査読

    2 被引用数 (Scopus)

    抄録

    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.

    本文言語English
    ページ(範囲)1555-1562
    ページ数8
    ジャーナルTetrahedron
    75
    11
    DOI
    出版ステータスPublished - 2019 3月 15

    ASJC Scopus subject areas

    • 生化学
    • 創薬
    • 有機化学

    フィンガープリント

    「Synthetic study of a moss-produced oxylipin and its structural revision」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

    引用スタイル