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

Abstract:

: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.

journal_name

J Chem Ecol

authors

Hedenström E,Andersson F

doi

10.1023/a:1016289902732

keywords:

subject

Has Abstract

pub_date

2002-06-01 00:00:00

pages

1237-54

issue

6

eissn

0098-0331

issn

1573-1561

journal_volume

28

pub_type

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