Texas leaf cutting ant

The Barton-Zard pyrrole synthesis has now been extensively applied to synthesis of natural and unnatural products containing pyrrole units. Methyl 4-methylpyrrole-2-carboxylate is the trail-maker pheromone of the Texas leaf-cutting ant Atta texana.24 It is readily prepared by the Barton Zard method in 60% yield (Eq. 10.22).22... 

Uses Mirex is used in North America and in the southeastern United States for the control of fire and ants. Mirex is also effective against the hamster ant, the yellow-jacket, the Texas leaf-cutting ant, and the Hawaiian mealy bug. A ban on the use of mirex for pest control with exemptions was brought in on June 30, 1978. It has its use as a fire retardant in plastics, rubber, paint, paper, and electrical goods from 1959 to 1972 due to its high melting point and high chemical stability.14,48... 

Methyl-3-heptanone (386a, Scheme 68), the alarm pheromone of the Texas leaf-cutting ant (Atta texana) was synthesized by Riley et al 173, 174) and required resolution of the intermediate, racemic 2-methyl-4-pentenoic acid (384). A convenient synthesis of methyl 4-methylpyrrole-2-carboxylate (392), the trail pheromone of A. texana, has been reported by Sonnet (775) (Scheme 69). Formylation of ester (390) with CUCHOMe and AICI3 gave predominantly the desired 4-formyl derivative (391). 

Sonnet, P. E. Synthesis of the trail marker of the Texas leaf-cutting ant, Atta texana (Buckley). J. Med. Chem. 15,97—98 (1972). 

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