Clerodane diterpenoids are widely distributed in nature and constitute one of the largest and, yet, still rapidly growing family of secondary metabolites. Of the relatively few clerodanes tested for biological activit...Clerodane diterpenoids are widely distributed in nature and constitute one of the largest and, yet, still rapidly growing family of secondary metabolites. Of the relatively few clerodanes tested for biological activity, many were found to possess interesting antifeedant and medicinal properties and are potentially useful as insecticidal, antitumour, antifungal, antibiotic, anti-peptic ulcer, and psychotropic agents. The structural complexity and biological activity associated with this class of natural products have attracted extensive effort towards their total synthesis. In most of the reported syntheses, the synthetic sequence is specific to the target molecule. We have recently developed a versatile synthetic approach which is applicable to the synthesis of a large number of target molecules with minor modifications. The key operation of this approach is the face-selective Diels-Alder reaction of dienone ester 1. The successful application of this approach has culminated in the total synthesis of several cisclerodane diterpenoids. We have since made considerable improvement on this general synthetic approach, in terms of the overall efficiency, making use of compounds 2 and 3 as dienophiles. This newly developed general synthetic approach towards clerodane diterpenoids will be presented.展开更多
文摘Clerodane diterpenoids are widely distributed in nature and constitute one of the largest and, yet, still rapidly growing family of secondary metabolites. Of the relatively few clerodanes tested for biological activity, many were found to possess interesting antifeedant and medicinal properties and are potentially useful as insecticidal, antitumour, antifungal, antibiotic, anti-peptic ulcer, and psychotropic agents. The structural complexity and biological activity associated with this class of natural products have attracted extensive effort towards their total synthesis. In most of the reported syntheses, the synthetic sequence is specific to the target molecule. We have recently developed a versatile synthetic approach which is applicable to the synthesis of a large number of target molecules with minor modifications. The key operation of this approach is the face-selective Diels-Alder reaction of dienone ester 1. The successful application of this approach has culminated in the total synthesis of several cisclerodane diterpenoids. We have since made considerable improvement on this general synthetic approach, in terms of the overall efficiency, making use of compounds 2 and 3 as dienophiles. This newly developed general synthetic approach towards clerodane diterpenoids will be presented.
