Total synthesis of racemic 2-desoxystemodinone and stemodinol; the identity of natural "stemodinol" with stemarin

Abstract

Total syntheses of the naturally occurring diterpenoid 2-desoxystemodinone (3) and the diterpenoid structure 2 ("stemodinol") are described. The synthetic diterpenoid 2 was not identical to an authentic sample of "stemodinol". The authentic sample was found to be stemarin to which structure 2 had been erroneously assigned in the literature. It would appear that the diterpenoid represented by 2 has not been isolated from natural sources.