Preparation of ketones from esters via substituted cyclopropanols. Application to the synthesis of (±)-ipsenol, (±)-ipsdienol and amitinol, the components of aggregation pheromones of the Ips bark beetles

Article abstract of DOI:10.1016/S0040-4020(99)00800-5

The regioselective two-step sequence of bromination- dehydrobromination of 2-(2,2-diethoxy)-1-methyl-1-cyclopropanol affords 3-(2,2-diethoxyethyl)-3-buten-2-one in high yield. The reduction of the latter, followed by chlorination and dehydrochlorinatiou, provides 2-(2,2-diethoxyethyl)-1,3-butadiene that was used as a building block for the synthesis of (±)- ipsenol, (±)ipsdienol and amitinol - the components of aggregation pheromones of the Ips bark beetles.