Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

• Adam Drop,
• Hubert Wojtasek and
• Bożena Frąckowiak-Wojtasek

Beilstein J. Org. Chem. 2020, 16, 616–620, doi:10.3762/bjoc.16.57

• unsymmetrically substituted cis-epoxides. The procedure was applied for the preparation of both enantiomers of disparlure and monachalure, the components of the sex pheromones of the gypsy moth (Lymantria dispar) and the nun moth (Lymantria monacha) using methyl (2S,3R,5R,6R)-3-ethylsulfanylcarbonyl-5,6-dimethoxy

• -5,6-dimethyl-1,4-dioxane-2-carboxylate as the starting material. Keywords: 2,3-butanediacetal; cis-epoxide; (−)-disparlure; (+)-disparlure; (−)-monachalure; (+)-monachalure; Introduction Compounds containing chiral epoxides display a wide range of biological activities and a number of them are

• ) and the nun moth (Lymantria monacha). The sex pheromone of the gypsy moth contains (+)-disparlure (1, (7R,8S)-7,8-epoxy-2-methyloctadecane) [10]. The pheromone blend of the nun moth contains (−)-disparlure (3, (7S,8R)-7,8-epoxy-2-methyloctadecane), (+)-monachalure (2, (7R,8S)-cis-7,8-epoxyoctadecane