Synthesis of bioactive sesquiterpene heliannuol E involving a ring-expansion reaction of spirodienones

Fuminao Doi, Takahisa Ogamino, Takeshi Sugai, Shigeru Nishiyama

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A heliannane-type sesquiterpene, heliannuol E (1), has been successfully synthesized. The key step was conversion of the electrochemically produced spiro compounds (8, and 18) into the corresponding dihydrobenzopyrans (11, 12, 19, and 20) by a selective ring expansion process.

Original languageEnglish
Pages (from-to)411-413
Number of pages3
JournalSynlett
Issue number3
Publication statusPublished - 2003

Fingerprint

Spiro Compounds
Chromans
Sesquiterpenes
heliannuol E

Keywords

  • Anodic oxidation
  • Dihydrobenzopyran
  • Heliannuol E
  • Sesquiterpene
  • Two-electron oxidation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of bioactive sesquiterpene heliannuol E involving a ring-expansion reaction of spirodienones. / Doi, Fuminao; Ogamino, Takahisa; Sugai, Takeshi; Nishiyama, Shigeru.

In: Synlett, No. 3, 2003, p. 411-413.

Research output: Contribution to journalArticle

Doi, Fuminao ; Ogamino, Takahisa ; Sugai, Takeshi ; Nishiyama, Shigeru. / Synthesis of bioactive sesquiterpene heliannuol E involving a ring-expansion reaction of spirodienones. In: Synlett. 2003 ; No. 3. pp. 411-413.
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