Conversion of 4-Oxoproline Esters to 4-Substituted Pyrrole-2-carboxylic Acid Esters

Yasushi Arakawa; Naomi Yagi; Yukimi Arakawa; Ken-ichi Tanaka; Shigeyuki Yoshifuji

doi:10.1248/cpb.57.167

Regular Articles

Conversion of 4-Oxoproline Esters to 4-Substituted Pyrrole-2-carboxylic Acid Esters

Yasushi Arakawa, Naomi Yagi, Yukimi Arakawa, Ken-ichi Tanaka, Shigeyuki Yoshifuji

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Keywords: 4-oxoproline ester, Grignard reaction, Horner–Emmons reaction, Reformatsky reaction, aromatization, methyl 4-methylpyrrole-2-carboxylate

JOURNAL FREE ACCESS

2009 Volume 57 Issue 2 Pages 167-176

DOI https://doi.org/10.1248/cpb.57.167

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Abstract

The Grignard, Wittig, Tebbe, Horner–Emmons, and Reformatsky reactions of the 4-oxoproline esters gave the corresponding 4-alylated or 4-alkylidenated products, respectively. The products were properly treated with bases to cause aromatization, giving 4-substituted pyrrole-2-carboxylic acid esters such as methyl 4-methylpyrrole-2-carboxylate, which is a trail pheromone of Atta texana.

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