Dienone-Phenol Rearrangement of (+ )-2,-Demethoxydehydrogriseofulvin into a 4-Methylxanthone Derivative

Taiko Oda, Yuko Yamaguchi, Yoshihiro Sato

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Treatment of (+)-2‘-demethoxydehydrogriseofulvin (2b) with magnesium iodide afforded 5-chloro-2,8-dihydroxy-6-methoxy-4-methylxanthone (3a) via dienone-phenol rearrangement. The structure of 3a was determined by means of a carbon-13 nuclear magnetic resonance (13C-NMR) long-range selective proton decoupling (LSPD) experiment performed on its diacetate 3b. The rearrangement of 2b was also effected with p-toluenesulfonic acid to give 5-chloro-6,8-dimethoxy-2-hydroxy-4-methylxanthone (6a). On the other hand, reaction of (— )-dehydrogriseofulvin (2d) with p-toluenesulfonic acid under more vigorous conditions resulted in racemization, no rearrangement being observed.

Original languageEnglish
Pages (from-to)858-863
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume34
Issue number2
DOIs
Publication statusPublished - 1986 Jan 1

Keywords

  • 13C-NMR long-range selective proton decoupling
  • 3-acetoxy-5-chloro-6,8-dimethoxy-1-methylxanthone
  • 5-chloro-2,8-diacetoxy-6-methoxy-4-methylxanthone
  • C-migration
  • dehydrogriseofulvin
  • dienone-phenol rearrangement
  • racemization

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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