title: 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.
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]
authors.affiliation: Department of Chemistry, University of Queensland, Brisbane, Australia.
authors.forename: Mary T
authors.initials: MT
authors.lastname: Fletcher
authors.forename: Sharon
authors.initials: S
authors.lastname: Chow
authors.forename: Lynette K
authors.initials: LK
authors.lastname: Lambert
authors.forename: Oliver P
authors.initials: OP
authors.lastname: Gallagher
authors.forename: Bronwen W
authors.initials: BW
authors.lastname: Cribb
authors.forename: Peter G
authors.initials: PG
authors.lastname: Allsopp
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Moore
authors.forename: William
authors.initials: W
authors.lastname: Kitching
mesh_terms: D000473:Alkanes / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D001517:Coleoptera / Q000737:chemistry*; D005260:Female; D006838:Hydrocarbons / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
chemical_list: C492633:4,6,8,10,16,18-hexamethyldocosane; C492632:4,6,8,10,16-pentamethyldocosane; D000473:Alkanes; D006838:Hydrocarbons