Synthesis of 2-acyl-3-chloropyrroles: Application to the synthesis of the trail pheromone of the ant Atta texana

Article abstract of DOI:10.1016/S0040-4020(99)00106-4

Alkyl 3-chloropyrrole-2-carboxylates and 2-alkanoyl-3-chloropyrroles are conveniently prepared from 2-alkyl-1-pyrrolines by tetra- and pentahalogenation with N-chlorosuccinimide, subsequent base-induced aromatisation with sodium alkoxides in the corresponding alcohol and final acid hydrolysis of the resulting orthoester or acetal functions into the 3- chloropyrrole. The developed strategy is applied to the synthesis of the trail pheromone of the ant Atta texana.