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

N. Kawai, Y. Fujibayashi, S. Kuwabara, Kenichi Takao, Y. Ijuin, S. 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
Publication statusPublished - 2000 Aug 25

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Programmable logic controllers
Stereochemistry
Ketones
Nuclear magnetic resonance
decalin
akaterpin

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Kawai, N., Fujibayashi, Y., Kuwabara, S., Takao, K., Ijuin, Y., & Kobayashi, S. (2000). Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC. Tetrahedron, 56(35), 6467-6478.

Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC. / Kawai, N.; Fujibayashi, Y.; Kuwabara, S.; Takao, Kenichi; Ijuin, Y.; Kobayashi, S.

In: Tetrahedron, Vol. 56, No. 35, 25.08.2000, p. 6467-6478.

Research output: Contribution to journalArticle

Kawai, N, Fujibayashi, Y, Kuwabara, S, Takao, K, Ijuin, Y & Kobayashi, S 2000, 'Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC', Tetrahedron, vol. 56, no. 35, pp. 6467-6478.
Kawai N, Fujibayashi Y, Kuwabara S, Takao K, Ijuin Y, Kobayashi S. Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC. Tetrahedron. 2000 Aug 25;56(35):6467-6478.
Kawai, N. ; Fujibayashi, Y. ; Kuwabara, S. ; Takao, Kenichi ; Ijuin, Y. ; Kobayashi, S. / Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC. In: Tetrahedron. 2000 ; Vol. 56, No. 35. pp. 6467-6478.
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