A Nine-Step Formal Synthesis of (±)-Morphine.

A nine-step stereoselective formal synthesis of (±)-morphine from readily available o-vanillin is presented. The carbocyclic structure of morphine was quickly assembled through an orchestration of the intermolecular Diels-Alder/Claisen/Friedel-Crafts sequential reaction. This approach involves many one-pot procedures and no protecting groups, and only a few chromatographic purifications are required.

Stereocontrolled glycoside synthesis by activation of glycosyl sulfone donors with scandium(iii) triflate.

The activation of aryl glycosyl sulfone donors has been achieved using scandium(iii) triflate and has led to the selective preparation of α-mannosides resulting from a post-glycosylation anomerization.