Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters |
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Authors: | Lourdes Muñoz Ma Pilar Bosch Gloria Rosell Angel Guerrero |
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Institution: | 1. Department of Biological Chemistry and Molecular Modelling, IQAC (CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain;2. Unit of Medicinal Chemistry (Associated to CSIC), Faculty of Pharmacy, University of Barcelona, Av. Diagonal, s/n, 08028 Barcelona, Spain |
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Abstract: | The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on a stereospecific alkylation with an alcohol-protected alkyl iodide using a pseudoephedrine derivative as a chiral auxiliary followed by subsequent removal of the auxiliary. Both enantiomers are obtained in excellent yields and enantioselectivities (93–94% ee). The strategy outlined allows preparation of a wide variety of enantiopure methyl-branched saturated and unsaturated fatty acids. |
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