A facile approach to cis- and trans-2-(l-hydroxymethyl)vinyl-1-vinylcyclohexan-1-ols and to the corresponding cyclopentane, cycloheptane, and cyclooctane derivatives has been developed, starting from cycloalkanones involving the key steps of Rupe and Claisen orthoester rearrangements. The formation of intervening products could be explained by allylic strain and π-stacking, respectively.
Memory of Chirality as a Prominent Pathway for the Synthesis of Natural Products through Chiral Intermediates