Stereospecific rearrangement of α-hydroxyepoxide: efficient approach to the trans-bicyclo[9.3.0]tetradecane core en route to clavulactone

We document a synthetic route to trans-bicyclo[9.3.0]tetradecanes. The strategy is based on a quantitative and stereospecific Lewis acid mediated rearrangement of α-hydroxyepoxide to β-hydroxyketone, which paved the way for the synthesis of clavulactone and clavirolides.