Syntheses of the sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol, including the (2S,3S,7S,11R) and (2S,3S,7S,11S) stereoisomers identified as pheromone precursors in females of the pine sawfly Microdiprion pallipes (Hymenoptera : Diprionidae).: Diprionidae)
2001 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 2, 353-363 p.Article in journal (Refereed) Published
All sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol were synthesised in high stereoisomerical purities (> 95%), for use in the identification of the stereoisomers present in females of the pine sawfly Microdiprion pallipes (Fallen) (Hymenoptera: Diprionidae) as the precursor of the actual sex pheromone (which is the propionate), and also for investigation of the biological activities of the esters. The key step in the syntheses was the coupling of each of the enantiomers of cis-3,4-dimethyl-gamma -butyrolactone with each of the four pure stereoisomers of 1-lithio-2,6-dimethyloctanes. The four corresponding alcohols were obtained by lipase-catalysed (Amano PS) kinetic separation, based on selective acylation of either (2R/S,6S)- or (2R/S,GR)-2,6-dimethyl-1-octanol (obtained from the optically pure enantiomers of citronellal). Additionally, a mixture of the 16 possible stereoisomers of 3,7,11-trimethyl-2-tridecanol was also prepared.
Place, publisher, year, edition, pages
2001. no 2, 353-363 p.
Asymmetric synthesis, Lipase, Microdiprion pallipes, Pheromones, Total synthesis, 3, 7, 11 trimethyl 2 tridecanol, alcohol, decanol, ester, gamma butyrolactone derivative, lactone derivative, octanol, propionic acid, sex pheromone, triacylglycerol lipase, unclassified drug, acylation, article, drug activity, enantiomer, enzyme kinetics, female, fly, Hymenoptera, nonhuman, stereoisomerism, synthesis
IdentifiersURN: urn:nbn:se:kth:diva-25543DOI: 10.1002/1099-0690(200101)2001:2<353ISI: 000166621900015OAI: oai:DiVA.org:kth-25543DiVA: diva2:359081
QC 201010262010-10-262010-10-262010-10-26Bibliographically approved