Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus
1995
Leal, W.S. | Shi, X. | Nakamuta, K. | Ono, M. (Masayuki) | Meinwald, J.
Male-released sex pheromone constituents of the longhorn beetle Anaglyptus subfasciatus (Coleoptera: Cerambycidae) are identified by GC-MS and GC-Fourier transform infrared as a 7:1 molar mixture of 3-hydroxy-2-hexanone and 3-hydroxy-2-octanone. These two compounds undergo thermal isomerization during GC analyses to give the corresponding 2-hydroxy-3-alkanones. Comparison of GC retention times of the natural products with those of synthesized enantiomerically pure compounds revealed that both semiochemicals have (R)-stereochemistry. These absolute configurations were confirmed by comparisons of the (R)-methoxy(trifluoromethyl)phenylacetic acid esters of insect-derived and synthetic samples.
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