Pheromones, III: A Simple Method to Direct the Reduction of α-Alkoxy-carbonyl Compounds

Article abstract of DOI:10.1007/BF00810831

Enantiomerically pure 1,2-diols bearing optionally syn or anti configurated secondary hydroxylic groups are synthesized from acetal-protected cyanohydrins.After resolution of the diastereomers the cyanohydrins are converted into α-alkoxy-ketones by Grignard-reaction followed by reduction using common chelating or non-chelating agents.Among others syntheses of enantiomerically pure pheromones, endo-Brevicomin, exo-Brevicomin and Dispalure are given as examples.