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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

Fletcher, M.T. and Chow, S. and Lambert, L.K. and Gallagher, O.P. and Cribb, B.W. and Allsopp, P.G. and 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
Deposited On:09 Jul 2004
Last Modified:07 Jun 2011 01:45

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