Novel cuticular hydrocarbons from the cane beetle Antitrogus parvulus--4,6,8,10,16-penta- and 4,6,8,10,16,18-hexamethyldocosanes-unprecedented anti-anti-anti-stereochemistry in the 4,6,8,10-methyltetrad.
The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus are 4,6,8,10,16-penta- and 4,6,8,10,16,18-hexamethyldocosanes, 1 and 2, respectively. Stereoisomers of 2,4,6,8-tetramethylundecanal of established relative stereochemistry were derived from 2,4,6-trimethylphenol and were then coupled with appropriate methyl-substituted phosphoranes 62 and 25 to furnish alkenes, which on reduction provided diastereomers of 1 and 2, respectively. Capillary gas chromatography, mass spectrometry, and high resolution 13C NMR spectroscopy confirmed 1 as either 84a or 84b and 2 as either 15a or 15b. The novelty of these structures and their relative stereochemistry is briefly related to polyketide assembly.
Chow
Sharon
S
Department of Chemistry, School of Molecular and Microbial Science, The University of Queensland, St. Lucia 4072, Australia.
Fletcher
Mary T
MT
Lambert
Lynette K
LK
Gallagher
Oliver P
OP
Moore
Christopher J
CJ
Cribb
Bronwen W
BW
Allsopp
Peter G
PG
Kitching
William
W
D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D001517:Coleoptera / Q000737:chemistry*; D005260:Female; D006838:Hydrocarbons / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
C492633:4,6,8,10,16,18-hexamethyldocosane; C492632:4,6,8,10,16-pentamethyldocosane; D000473:Alkanes; D006838:Hydrocarbons