Sugar allyltins in the synthesis of carbohydrate mimics. Study on the cis-hydroxylation of the bicyclo[4.3.0]nonenes derived from d-mannose

Sugar allyltin derivatives were applied in the synthesis of highly oxygenated hydrindane system. The transformation of organometallic derived from d-mannose into two diastereoisomeric bicyclo[4.3.0]nonenes with the trans geometry between both the rings was realized in a few well-defined steps. The functionalization of these synthons provided a wide range of polyhydroxylated hydrindane derivatives. The stereochemical aspects of these processes are discussed.