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
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
复制标题
DOI：
10.1021/jo0481093
复制
发表时间：
2005-03-04
影响因子：
3.6
通讯作者：
Kitching, W
中科院分区：
文献类型：
--
作者：
Chow, S;Fletcher, MT;Kitching, W
[图表]甘蔗甲虫物种小反甲的主要表皮烃是4，6，8，10，16-五和4，6，8，10，16，18-六甲基二十二烷，分别为I和2。从2，4，6-三甲基苯酚衍生出具有确定的相对立体化学的2，4，6，8-四甲基十一醛的立体异构体，然后与适当的甲基取代的正膦62和25偶联得到烯烃，其在还原时分别得到I和2的非对映异构体。毛细管气相色谱、质谱和高分辨率C-13 NMR光谱证实1为84 a或84 b，2为15 a或15 b。这些结构的新奇和它们的相对立体化学简单地与聚酮组装有关。
[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.