Synthesis of highly oxygenated bicyclo[4.3.0]nonanes from sugar allyltins: model transformations of the adduct derived from the d-mannose

Sugar allyltin, a derivative of the d-mannose, was converted in a few well-defined steps into the bicyclic precursor of fully oxygenated hydrindane. Selective transformations of this precursor into the bicyclic derivatives containing the azido functionality are presented. The previously assigned structure of the bicyclic skeleton is also corrected.