Facile synthesis of tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones from phenols with an olefin bearing an electron-attracting group at the side chain

Shojiro Maki, Seiji Kosemura, Shosuke Yamamura, Shigeru Ohba

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

3,4-Dimethoxyphenol with a trans p-nitrostyryl group at the side chain was electrolyzed in acetic anhydride containing nBu4NBF4 to afford a tricyclo[5.3.1.01,5]undec-9-ene-8,11-dione, while the cis isomer was converted into a tricyclo[5.4.0.01,5]undec-9-ene-8,11-dione as a major product. In the case of several phenols with an α,β-unsaturated ketone or ester grouping, the corresponding tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones were also obtained in good yields.

Original languageEnglish
Pages (from-to)6083-6086
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number38
DOIs
Publication statusPublished - 1993 Sep 17

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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