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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
- 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
- Description:
- 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]
- 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.
