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

1 Citation (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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