Stereochemistry of Knoevenagel Condensation Products from Cyanoacetates and Aromatic Aldehydes

Hidetsura Cho, Takashi Iwashita, Mikiko Hamaguchi, Yoshiaki Oyama

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The C-13 long-range selective proton decoupling method and X-ray crystallographic analysis were employed to determine the stereochemistry of the caffeic acid derivatives, extremely potent 12-lipoxygenase inhibitors, synthesized from cyanoacetates and aromatic aldehydes. The ester group of 1 and 2 was found to be trans to the phenyl group.

Original languageEnglish
Pages (from-to)3341-3342
Number of pages2
JournalChemical and Pharmaceutical Bulletin
Volume39
Issue number12
DOIs
Publication statusPublished - 1991

Keywords

  • 12-lipoxygenase
  • 12-lipoxygenase inhibitor
  • C-13 NMR long-range selective proton decoupling (LSPD)
  • E-regioisomer
  • Keywords stereochemistry
  • Knoevenagel condensation
  • X-ray crystallographic analysis
  • Z-regioisomer
  • caffeic acid derivative
  • regioselectivity

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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