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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

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

Mary T Fletcher, Sharon Chow, Lynette K Lambert, Oliver P Gallagher, Bronwen W Cribb, Peter G Allsopp, Christopher J Moore, William Kitching

Org Lett. 2003 Dec 25;5(26):5083-6.

PMID: 14682770

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]

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP527606	2,4,6-Trimethylphenol		527-60-6	Price

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