Synthesis of chiral hexasubstituted cyclohexanediol, a key intermediate for the synthesis of verticillol, from (+)-dihydrocarvone; attempted cyclization to 12-membered carbocycle in verticillol using RCM reaction

Abstract

A cyclohexane derivative with three chiral centers, a key intermediate for the synthesis of a diterpene verticillol, was prepared starting from (+)-dihydrocarvone. A further challenge to cyclize to a 12-membered carbocycle was attempted, although the products were dimeric derivatives presumably due to an undesirable conformation of the substrate.