Patrick Perlmutter Pages 139 - 152 ( 14 )
Many bio-active compounds contain one or more saturated or partially saturated heterocycles. Most of these contain one or more stereo centres. As a result any attempts to synthesize these compounds must take full account of the stereochemistry. In this article a new approach to the stereoselective synthesis of heterocycles is reviewed. The emphasis is on oxygen-containing heterocycles. The approach involves a sequence of a nucleophilic addition reaction followed by an electrophilic ring closure. Examples are given of the stereoselective synthesis of the heterocyclic subunits of macrolide and polyether antibiotics, γ-butyrolactone autoregulators, marine polyether toxins and C-glycosides.