Unsaturated carbohydrates. Part 25. Abbreviated synthesis of the insect pheromone (+)-exo-brevicomin from a nona-3,8-dienulose derivative
Abstract
The insect pheromone (+)-exo-brevicomin (9) has been synthesised from the methyl 6-deoxy-6-iodo-α-D-glucopyranoside derivative (1) in 54% yield by way of the dienone (5) from which the ketone (7) was obtained by concurrent hydrogenation of the double bonds and hydrogenolysis of the allylic ester group.