Synthesis of Monomorin I, a Trail Pheromone of the Pharao Ant (Monomorium pharaonis) Katalytic hydrogenation of the 4‐nitroalkanone 5 yielded the cis‐pyrrolidine ester 6 (Scheme). The preparation of 5 was accomplished by ethanolysis of the nitrocyclohexanone derivative 4. Iodination at C(α) of 6, followed by cyclization, gave a nearly 5:6 mixture of the two C(5)‐epimers 10/9 of octahydroindolizine. Epimerisation of the undesired 10 to 9 and subsequent transformation of the latter gave racemic monomorine I (1; 34% yield from 5).
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Vavrecka et al. (1991) studied this question.
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