Epimerization of tilivalline

Takatoshi Matsumoto, Nobuyuki Matsunaga, Ayako Kanai, Toyohiko Aoyama, Takayuki Shioiri, Eiji Osawa

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Epimerization of tilivalline (1) at the C11-position occurred by treatment with zinc chloride to give a mixture of 1 and its 11-epimer (epi-1) in a ratio of 83 : 17. The computational chemical analysis of the thermodynamic stability of 1 and epi-1 through MM3(92) also revealed the energetic preference of 1 and the calculated equilibrium ratio of 1 and epi-1 was consistent with the experimental results. The torsional and bending angle parameters around the amide bond were determined.

Original languageEnglish
Pages (from-to)9781-9788
Number of pages8
JournalTetrahedron
Volume50
Issue number32
DOIs
Publication statusPublished - 1994
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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