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, antipeptic ulcer, and psychotropic agents. The structural complexity and biological activity associated with this class of natural products have attracted extensive effort towards their total syntheses. In most of the reported syntheses, the synthetic sequence is specific to the target molecule. We have recently developed an efficient general strategy for the synthesis of clerodane diterpenoids of the cis-series. The key ingredient is the face selective Diels-Alder reaction of dienophile 1. The successful application of this strategy has culminated in the first total synthesis of the naturally occurring compounds solidagolactones IV (2) and V (3) in racemic form.
Date:
2007-03
Relation:
Abstracts of Papers - American Chemical Society. 2007 Mar;233:407-ORGN.
