We will report our efforts toward the synthesis of the diasteromeric natural products <i>exo</i>- and <i>endo</i>-brevicomin, which are both insect pheromones. Our proposed synthesis utilizes cross metathesis to construct an acylic keto diol precursor, which we anticpate will undergo rhenium-catalyzed allylic transposition to produce a cyclic hemiacetal intermediate. A second allylic transposition is expected to produce the bicyclic acetal skeleton of our targets. Completion of the synthesis would then require only a single hydrogenation step. If succesful, our route would provide easy acces to these natural products and demonstrate the utility of this double allylic transposition strategy for the preparation of bicyclic acetals.

Synthetic studies on brevicomin

255th National Meeting (2018)

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