ISSN:
0947-3440
Keywords:
Ants
;
Alkaloids
;
Myrmicaria eumenoides
;
3-Butyl-5-(1-oxopropyl)indolizidine, (3R,5S,9R)-,(3R,5R,9R)-
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The (3R,5S,9R) and (3R,5R,9R) stereoisomers of 3-butyl-5-(1-oxopropyl)indolizidine (9) were identified as major constituents of the poison gland secretion of the African ant, Myrmicaria eumenoides. Racemates of the four diastereomers of 9 were synthesized via the corresponding ethyl 5-(5-butylpyrrolidin-2-yl)pentanoates (6). Enantiomerically pure samples of the (3R)-stereoisomers of 9 were obtained by starting from (2R)-2,3-O-isopropylideneglyceric aldehyde (21) and 6-methylpyridine-2-carboxaldehyde (20). In addition, the enantiomeric separation by chiral gas chromatography and unambiguous structure assignment of the target compounds are described.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199506138
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