Pheromone synthesis. Part 245: Synthesis and chromatographic analysis of the four stereoisomers of 4, 8-dimethyldecanal, the male aggregation pheromone of the …

K Akasaka, S Tamogami, RW Beeman, K Mori

Index: Akasaka, Kazuaki; Tamogami, Shigeyuki; Beeman, Richard W.; Mori, Kenji Tetrahedron, 2011 , vol. 67, # 1 p. 201 - 209

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Citation Number: 18

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 ...