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

作者：Akasaka Kazuaki; Tamogami Shigeyuki; Beeman Richard W; Mori Kenji^*

来源：Tetrahedron, 2011, 67(1): 201-209.

DOI：10.1016/j.tet.2010.10.086

• 4,8-Dimethyldecanal
• GC, Enantiomer separation
• HPLC, Diastereomer separation
• Pheromone
• Tribolium castaneum
• Tribolure

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 (45,8R)-1 and (4S,8S)-1, when octakis-(2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin was employed as a chiral stationary phase. Complete separation of the four stereoisomers of 1 on reversed-phase HPLC at -54 degrees 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.

• 出版日期2011-1-7