Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax

被引：10

作者：

Mori, K

Ohtaki, T

Ohrui, H

Berkebile, DR

Carlson, DA

机构：

[1] Fuji Flavor Co Ltd, Insect Pheromone & Traps Div, Hamura, Tokyo 2058503, Japan

[2] Tohoku Univ, Grad Sch Life Sci, Aoba Ku, Sendai, Miyagi 9818555, Japan

[3] ARS, USDA, Midw Livestock Insect Res Unit, Lincoln, NE 68583 USA

[4] ARS, USDA, Ctr Med Agr & Vet Entomol, Gainesville, FL 32611 USA

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2004年 / 68卷 / 08期

关键词：

Cochliomyia hominivorax; enzymatic kinetic resolution; lipase; methyl-branched secondary acetate; pheromone;

D O I：

10.1271/bbb.68.1768

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The four stereoisomers of 7-acetoxy-15-methylnonacosane (1), a component of the female sex pheromone of the New World screwworm fly (Cochliomyia hominivorax) were synthesized. The stereogenic center at C-15 of 1 originated from that of the enantiomers of citronellal, and that at C-7 was generated by lipase-catalyzed asymmetric acetylation of (3RS,11R)- and (3RS,11S)-17-methyl-1-trimethylsilylpentacos-1-yn-3-ol (13). Three of the stereoisomers of 1 showed equivalent good pheromone activity, while the activity of (7R,15R)-1 was weak.

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页码：1768 / 1778

页数：11

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