Kenneth B. Lipkowitz

Studies Directed Towards a Practical Synthesis of Brevicomins (II)1 : A Novel Synthesis of 1, 5-Dimethyl-8-Oxobicyclo [3.2.1]octane-6-one

Abstract The recent interest in pheromones,2 as means of controlling insect pests, has prompted us to examine syntheses which could be both simple and practical. We recently reported a three-step synthesis of brevicomin (3), the aggregating pheromone of the pine bark beetle, Dendroctonus brevicomis.3

Studies Directed Towards a Practical Synthesis of Brevicomin (III) Cyclization Routes to 6, 8-Dioxabicyclo[3.2.1]octane

Abstract Bicyclic ketals have been noted as an important structural unit in sugars1, an alkaloid2, a terpene3 and in pheromones. It is with regard to this last group that we have been recently directing our attention. Frontalin (1)4 and the brevicomins (2 and 3)5 are sex aggregating pheromones of Dendroctonus frontalisand D. brevicomis, respectively. Because of their potential utility in controlling populations of pine bark beetles, considerable activity has been directed towards their syntheses. 6–10 Particularly in syntheses of brevicomin, where the exo-isomer (2) is the biologically useful isomer for insect control, does the methodology become quite important.