Synthesis of Pinguisane-Type Sesquiterpenoids Acutifolone A,Pinguisenol,and Bisacutifolones by a Diels-Alder Dimerization Reaction

摘要

The total synthesis of pinguisane-type sesquiterpenoids,acutifolone A (1) and pinguisenol (2),has been achieved by using the Mukaiyama aldol reaction as the key step.The intermolecular Diels-Alder reaction of these monomelic natural products successfully led to stereoselective dimerization,leading to bisacutifolones A (3) and B (4).Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state.