Process for producing acosamine, daunosamine, 1-thioacosamine and related compounds

摘要

A process for synthesizing acosamine, daunosamine and 1-thioacosamines from L-rhamnal is disclosed that can generally be characterized by Michael addition of an alkoxide or thioalkoxide to the enone formed by allylic oxidation of L-rhamnal to directly generate the 2-deoxy functionality, and stereospecific reduction of the oxime to the arabino compound which establishes configuration at C-3 and generates a compound which requires only epirmerization at C-4 to yield the desired product. The synthesis of anthracycline antibiotics incorporating these sugars or their derivatives by glycosidation of the glycone is also disclosed.