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Pheromone synthesis. Part 245: Synthesis and chromatographic analysis of the four stereoisomers of 4,8-dimethyldecanal, the male aggregation pheromone of the red flour beetle, Tribolium castaneum

Permanent URL:
http://handle.nal.usda.gov/10113/49944
Abstract:
All four stereoisomers of 4,8-dimethyldecanal (1) were synthesized from the enantiomers of 2-methyl-1-butanol and citronellal. Enantioselective GC analysis enabled separation of (4R,8R)-1 and (4R,8S)-1 from a mixture of (4S,8R)-1 and (4S,8S)-1, when octakis-(2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl)-γ-cyclodextrin was employed as a chiral stationary phase. Complete separation of the four stereoisomers of 1 on reversed-phase HPLC at −54 °C was achieved after oxidation of 1 to the corresponding carboxylic acid 12 followed by its derivatization with (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanol, and the natural 1 was found to be a mixture of all the four stereoisomers.
Author(s):
Akasaka, Kazuaki , Tamogami, Shigeyuki , Beeman, Richard W. , Mori, Kenji
Subject(s):
Tribolium castaneum , stereoisomers , insect pheromones , aggregation pheromones , aldehydes , chemical analysis , reversed-phase high performance liquid chromatography
Format:
p. 201-209.
Note:
Includes references
Source:
Tetrahedron 2011 Jan. 7, v. 67, no. 1
Language:
English
Year:
2011
Collection:
Journal Articles, USDA Authors, Peer-Reviewed
File:
Download [PDF File]
Rights:
Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted.