4,6,8,10,16-penta- and 4,6,8,10,16,18-hexamethyldocosanes from the cane beetle Antitrogus parvulus -: Cuticular hydrocarbons with unprecedented structure and stereochemistry

被引：33

作者：

Fletcher, MT ^{[1
]}

Chow, S

Lambert, LK

Gallagher, OP

Cribb, BW

Allsopp, PG

Moore, CJ

Kitching, W

机构：

[1] Univ Queensland, Dept Chem, Brisbane, Qld, Australia

[2] Univ Queensland, Dept Zool & Entomol, Brisbane, Qld, Australia

[3] Univ Queensland, Ctr Magnet Resonance, Brisbane, Qld, Australia

[4] BSES Ltd, Indooroopilly, Qld, Australia

[5] Dept Primary Ind, Yeerongpilly, Qld, Australia

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 26期

关键词：

D O I：

10.1021/ol0361453

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 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.

引用

页码：5083 / 5086

页数：4

共 17 条

[1] Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary [J].