Preparation of 8-methyl-2-decanol: General synthesis of diastereomeric mixtures of alkyl branched insect pheromones
- 1 August 1987
- journal article
- research article
- Published by Springer Nature in Journal of Chemical Ecology
- Vol. 13 (8) , 1927-1933
- https://doi.org/10.1007/bf01013241
Abstract
A general method for synthesis of insect pheromones having alkyl branched carbon skeletons is demonstrated with the preparation of a diastereomeric mixture of 8-methyl-2-decanol, whose propionate is an attractant of someDiabrotica species. The procedure involves reaction of a ketone with lithium acetylide ethylenediamine complex to afford a propargylic alcohol containing the branch of the target molecule. Copper (1) mediated alkylation of the derived propargylic acetate with a primary alkyl halide yields a trisubstituted allene having the desired chain length, and isomerization with an alkali metal amide of either ethylenediamine or 1,3-diaminopropane, affords the alkyl branched terminal acetylene. The triple bond is converted to the methyl ketone and reduced to the methyl carbinol. The reactions proceed in good yield, and can be conveniently carried out on large scale. The method should prove useful for production of pheromone components in cases where diastereomeric mixtures can be employed.This publication has 15 references indexed in Scilit:
- Deuteration of cycloalkynesTetrahedron Letters, 1985
- Response of northern corn rootworm,Diabrotica barberi Smith and Lawrence, to stereoisomers of 8-methyl-2-decyl propanoateJournal of Chemical Ecology, 1985
- Response ofDiabrotica virgifera virgifera, D. v. Zeae, andD. porracea to stereoisomers of 8-methyl-2-decyl propanoateJournal of Chemical Ecology, 1984
- Synthesis of the propionates of (2r, 8r)- and (2s, 8r)-8-methyl-2-decanol, the pheromone of the western corn rootworm, employing chiral compounds of microbial origin as starting materialsTetrahedron, 1984
- Identification of a female-produced sex pheromone from the southern corn rootworm,Diabrotica undecimpunctata howardi BarberJournal of Chemical Ecology, 1983
- Isomerization of acetylenic acids with sodium salt of 1,2-diaminoethane: a one step synthesis of megatomoic acidCanadian Journal of Chemistry, 1982
- Identification of a female-produced sex pheromone of the western corn rootwormJournal of Chemical Ecology, 1982
- A general synthesis of long chain ω- and (ω-1)-hydroxy fatty acidsChemistry and Physics of Lipids, 1981
- Synthesis of optically active forms of (Z)-14-methylhexadec-8-enalTetrahedron, 1978
- Saline hydrides and superbases in organic reactions. IX. Acetylene zipper. Exceptionally facile contrathermodynamic multipositional isomeriazation of alkynes with potassium 3-aminopropylamideJournal of the American Chemical Society, 1975