Abstract:

Frontalin, the pheromone of Dendroctonus Bark Beetles, was first isolated by Kinzer^[1] from hindgut extracts of male western pine beetles. Its structure was determined as 1,5-dimethyl-6,8-dioxabicyclo[3.2.1] octane (1) by spectral analysis and was confirmed by the synthesis of its racemate^[1,2]. On account of its structural novelty and economic value, this compound has been studied extensively ^[3-5]. But most of its synthetic methods required relatively longer steps or suffered from the inaccessibility of starting materials or reagents. Now, we report a convenient synthetic method for (±)-frontalin starting from easily available material, natural unsaturated aliphatic aicd, oleic acid. The synthesis is shown in scheme.