Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC

Nobuyuki Kawai, Yuko Fujibayashi, Seiya Kuwabara, Ken Ichi Takao, Yasuharu Ijuin, Susumu Kobayashi

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and trans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of β,γ-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)6467-6478
Number of pages12
JournalTetrahedron
Volume56
Issue number35
DOIs
Publication statusPublished - 2000 Aug 25

Keywords

  • Akaterpin
  • Cis-decalin
  • Intramolecular Diels-Alder
  • Trans-decalin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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