title: Conversion of 4-oxoproline esters to 4-substituted pyrrole-2-carboxylic acid esters.
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.
authors.affiliation: Hokuriku University, Kanazawa, Japan. ya-arakawa@hokuriku-u.ac.jp
authors.forename: Yasushi
authors.initials: Y
authors.lastname: Arakawa
authors.forename: Naomi
authors.initials: N
authors.lastname: Yagi
authors.forename: Yukimi
authors.initials: Y
authors.lastname: Arakawa
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Tanaka
authors.forename: Shigeyuki
authors.initials: S
authors.lastname: Yoshifuji
mesh_terms: D000478:Alkylation; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010675:Pheromones / Q000737:chemistry; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D010675:Pheromones; D011761:Pyrrolidonecarboxylic Acid