A novel (5E,9Z)-dialkylindolizidine from the ant Monomorium smithii.
The alkaloidal venom of Monomorium smithii was found to contain (5E,9Z)-3-butyl-5-(4-penten-1-yl)indolizidine [1b], a novel indolizidine, its monocyclic analogue trans-2-butyl-5-(8-nonen-1-yl)pyrrolidine [2], (5E,8Z)-3,5-di(5-hexen-1-yl)pyrrolizidine [3], and trans-2-(5-hexen-1-yl)-5-(8-nonen-1-yl)pyrrolidine [4]. The structure of 1b was based on the results of two independent syntheses. Reductive amination of the appropriate triketone confirmed the carbon-nitrogen skeleton of 1b and suggested its stereochemistry, which was verified by the results of a stereoselective synthesis based on pyrrole hydrogenation. The chemotaxonomic implications of this first report of the concomitance of a 3,5-dialkylindolizidine and a 3,5-dialkylpyrrolizidine in an ant venom are discussed.
Jones
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TH
Laboratory of Chemistry, National Heart, Lung and Blood Institute, Bethesda, Maryland 20892.
Laddago
A
A
Don
A W
AW
Blum
M S
MS
D000470:Alkaloids / Q000032:analysis; D000862:Ant Venoms / Q000032:analysis*; D001180:Arthropod Venoms / Q000032:analysis*; D055598:Chemical Phenomena; D002621:Chemistry; D007212:Indolizines / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy
D000470:Alkaloids; D000862:Ant Venoms; D001180:Arthropod Venoms; D007212:Indolizines; C064678:3-butyl-5-(4-penten-1-yl)indolizidine