Syntheses of female sex pheromone precursors of pine sawfly species and of some structurally related methyl-branched long-chain 2-alkanols

被引：14

作者：

Hedenström, E ^{[1
]}

Andersson, F ^{[1
]}

机构：

[1] Mid Sweden Univ, Dept Nat & Environm Sci, SE-85170 Sundsvall, Sweden

来源：

JOURNAL OF CHEMICAL ECOLOGY | 2002年 / 28卷 / 06期

关键词：

sex pheromone; pine sawfly; synthesis; Diprion nipponica; Macrodiprion nemoralis; Microdiprion pallipes;

D O I：

10.1023/A:1016289902732

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：

3,7-Dimethyl-2-undecanol, 3,7,9-trimethyl-2-tridecanol, and 3,7, 11-trimethyl-2-tridecanol were synthesized as racemic mixtures in moderate yields. The alcohols are known precursors of the female sex pheromones of the pine sawfly species Diprion nipponica, Macrodiprion nemoralis, and Microdiprion pallipes, respectively. Stereoisomeric mixtures of 3,8,12-trimethyl-2-tridecanol, erythro-(2R;3R;11R/S)-3,11-dimethyl-2-tetradecanol, 3,5-dimethyl-2-tetradecanol, and 5,7-dimethyl-2-tetradecanol, structurally related to sex pheromone alcohol precursors of pine sawfly species, were also synthesized in moderate yields. The key reaction in the syntheses was the ring opening of gamma-butyrolactones by using different alkyl lithiums as nucleophiles.

引用

页码：1237 / 1254

页数：18

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