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Synthese von Monomorin I, einem Spurpheromon der Pharao‐Ameise ( Monomorium pharaonis )
Author(s) -
Vavrecka Mojmir,
Hesse Manfred
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740221
Subject(s) - chemistry , epimer , pyrrolidine , stereochemistry , halogenation , yield (engineering) , organic chemistry , materials science , metallurgy
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 ).