Stereoselective Synthesis of Taxane Derivatives

Article abstract of DOI:10.1002/hlca.19890720113

Substituted racemic 4,8,12-trinortaxanes were prepared stereoselectively in several steps from the dienone 10.A variant of the de Mayo reaction with bicyclononenones 4 and cyclohexen produced the desired configuration at C(8) of the taxane framework.Retro-aldol cleavage of the tetracycle 5 led to the taxane skeleton 6.Stereoselective reduction followed by treatment with base afforded 7b.Hydrolysis of the acetal group and further reduction yielded 9 in which the relative configuration corresponds to the one of the natural products.