Synthesis of Diaprepal A₂ Cadinane Analogs; Efficient Access to Polyoxygenated Cadinanes

Abstract

Synthesis of the cadinane skeleton using Robinson annelation as key step is described; the use of the α-hydroxy methylene derivative of dihydro carvone allowed a good control of the regiochemistry of the reaction; synthesis of2b and 2c is possible using carvone as starting ketone; generalization of this procedure to epoxide 15 is also described leading to polyoxygenated cadinanes.