A Stereoselective Synthesis of Brevicomin

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Abstract
Silverstein and his coworkers1 have reported the isolation of brevicomin, the principal aggregation pheromone from the frass produced by the female Hestern pine beetle Derdroctonus brevicomis, and assigned its structure as exo-7-ethyl-5-methyl-6,8- dioxabicyclo[3,2,1]octane (1). Several reports describing its synthesis have appeared1,2 because of its novel structural feature as well as its usefulness for the protection of the pine tree. Me wish to delineate its synthesis from a readily available starting material tetrahydrofurfuryl alcohol.