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

Takashi Yatsunami; Shuichi Furuya; Toshihiko Okamoto

doi:10.1248/cpb.26.3199

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

Takashi Yatsunami, Shuichi Furuya, Toshihiko Okamoto

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	3199-3207
Number of pages	9
Journal	Chemical and Pharmaceutical Bulletin
Volume	26
Issue number	10
DOIs	https://doi.org/10.1248/cpb.26.3199
Publication status	Published - 1978
Externally published	Yes

Keywords

aconitum
chloramine
diterpene alkaloid
fragmentation reaction
intramolecular Grignard reaction
kobusine

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.26.3199

Cite this

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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.",

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