Chemical Conversion of Kobusine. Cleavage and Regeneration of the Bridged C14-C20Bond

Takashi Yatsunami, Shuichi Furuya, Toshihiko Okamoto

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

An aconite alkaloid, kobusine (1) was converted to a C14-C20 bond cleaved derivative (12) by a novel fragmentation reaction via a chloramine (11). Possible mechanisms were discussed in which participation of anionic nitrogen was proposed. The C14-C20 bond regeneration in compound (12) was also accomplished by an intramolecular Grignard type reaction.

Original languageEnglish
Pages (from-to)3199-3207
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume26
Issue number10
DOIs
Publication statusPublished - 1978
Externally publishedYes

Keywords

  • aconitum
  • chloramine
  • diterpene alkaloid
  • fragmentation reaction
  • intramolecular Grignard reaction
  • kobusine

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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