4,6,8,10,16-Penta- and 4,6,8,10,16,18-hexamethyldocosanes from the cane beetle Antitrogus parvulus - Cuticular hydrocarbons with unprecedented structure and stereochemistry

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Fletcher, M.T., Chow, S., Lambert, L.K., Gallagher, O.P., Cribb, B.W., Allsopp, P.G., Moore, C.J. and Kitching, W. (2003) 4,6,8,10,16-Penta- and 4,6,8,10,16,18-hexamethyldocosanes from the cane beetle Antitrogus parvulus - Cuticular hydrocarbons with unprecedented structure and stereochemistry. Organic Letters, 5 (26). pp. 5083-5086.

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Abstract

The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus were deduced to be 4,6,8,10,16,18-hexa- and 4,6,8,10,16- pentamethyldocosanes 2 and 3, respectively. Isomers of 2,4,6,8-tetramethylundecanal 27, 36, and 37, derived from 2,4,6-trimethylphenol, were coupled with the phosphoranes 28 and 29 to furnish alkenes and, by reduction, diastereomers of 2 and 3. Chromatographic and spectroscopic comparisons confirmed 2 as either 6a or 6b and 3 as either 34a or 34b.

Item Type:	Article
Corporate Creators:	Biosecurity Queensland
Additional Information:	© American Chemical Society.
Keywords:	Scarab beetles; pests; sugarcane crops.
Subjects:	Science > Physiology > Insect biochemistry
Live Archive:	09 Jul 2004
Last Modified:	03 Sep 2021 16:47

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