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.
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]
Fletcher
Mary T
MT
Department of Chemistry, University of Queensland, Brisbane, Australia.
Chow
Sharon
S
Lambert
Lynette K
LK
Gallagher
Oliver P
OP
Cribb
Bronwen W
BW
Allsopp
Peter G
PG
Moore
Christopher J
CJ
Kitching
William
W
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
C492633:4,6,8,10,16,18-hexamethyldocosane; C492632:4,6,8,10,16-pentamethyldocosane; D000473:Alkanes; D006838:Hydrocarbons