4,6,8,10,16-penta- and 4,6,8,10,16,18-hexamethyldocosanes from the cane beetle antitrogusparvulus--cuticular hydrocarbons with unprecedented structure and stereochemistry |
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Authors: | Fletcher Mary T Chow Sharon Lambert Lynette K Gallagher Oliver P Cribb Bronwen W Allsopp Peter G Moore Christopher J Kitching William |
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Affiliation: | Department of Chemistry, University of Queensland, Brisbane, Australia. |
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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. [structure: see text] |
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