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


Autoria(s): Chow, Sharon; Fletcher, Mary T.; Lambert, Lynette K.; Gallagher, Oliver P.; Moore, Christopher J.; Cribb, Bronwen W.; Allsopp, Peter G.; Kitching, William
Data(s)

01/01/2005

Resumo

[GRAPHICS] 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, I 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 I and 2, respectively. Capillary gas chromatography, mass spectrometry, and high resolution C-13 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.

Identificador

http://espace.library.uq.edu.au/view/UQ:76298

Idioma(s)

eng

Publicador

Amer Chemical Soc

Palavras-Chave #Chemistry, Organic #Nmr Chemical-shifts #Scarab Beetles #Aggregation Pheromone #Lardoglyphus-konoi #Acarid Mite #Conformation #Configuration #Polypropylene #Melolonthinae #Coleoptera #C1 #250301 Organic Chemical Synthesis #250302 Biological and Medical Chemistry #780103 Chemical sciences #0305 Organic Chemistry
Tipo

Journal Article