Syntheses of female sex pheromone precursors of pine sawfly species and of some structurally related methyl-branched long-chain 2-alkanols.
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.
Chemistry Department of Natural and Environmental Sciences, Mid Sweden University, Sundsvall. erik.hedenstrom@mh.se
Erik
E
Hedenström
Fredrik
F
Andersson
D000473:Alkanes / Q000737:chemistry*; D000818:Animals; D005260:Female; D012739:Gonadal Steroid Hormones / Q000138:chemical synthesis*; D006927:Hymenoptera / Q000737:chemistry*; D008297:Male; D013045:Species Specificity; D013057:Spectrum Analysis
D000473:Alkanes; D012739:Gonadal Steroid Hormones