Enantioselective synthesis of heliannuol E; structural consideration of natural molecule

Fuminao Doi, Takahisa Ogamino, Takeshi Sugai, Shigeru Nishiyama

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms, by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position.

Original languageEnglish
Pages (from-to)4877-4880
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number26
DOIs
Publication statusPublished - 2003 Jun 23

Keywords

  • Allelopathy
  • Heliannuol E
  • Helianthus annuus L. cv. SH-222
  • Phenolic oxidation
  • Ring expansion
  • Spirodienone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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