Stereochemistry of Knoevenagel Condensation Products from Cyanoacetates and Aromatic Aldehydes

Hidetsura CHO; Takashi IWASHITA; Mikiko HAMAGUCHI; Yoshiaki OYAMA

doi:10.1248/cpb.39.3341

Hidetsura CHO, Takashi IWASHITA, Mikiko HAMAGUCHI, Yoshiaki OYAMA

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

JOURNAL FREE ACCESS

1991 Volume 39 Issue 12 Pages 3341-3342

DOI https://doi.org/10.1248/cpb.39.3341

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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.

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