Synthesis of dihydropyrroles by the intramolecular addition of alkylideneaminyl radicals generated from O-2,4-dinitrophenyloximes of γ,δ- unsaturated ketones

Katsuya Uchiyama, Yujiro Hayashi, Koichi Narasaka

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

Alkylideneaminyl radicals are generated from O-2,4-dinitrophenyloximes of γ,δ-unsaturated ketones by treatment with NaH and 3,4- methylenedioxyphenol. The resulting radical species successively add to the olefinic moiety intramolecularly to afford dihydropyrroles in the presence of a radical trapping agent. This method is applied for the stereoselective synthesis of xenovenine, a bicyclic 3,5-dialkylpyrrolizidine alkaloid.

Original languageEnglish
Pages (from-to)8915-8930
Number of pages16
JournalTetrahedron
Volume55
Issue number29
DOIs
Publication statusPublished - 1999 Jul 16
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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