Abstract
| - A systematic approach to the regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols arising from tetra-O-benzylconduritol B epoxide (9) and its aziridine analogue22, respectively, is described. In all cases, the synthetic methodologies rely on the regio- andstereocontrolled azidolysis of the starting precursors to give the corresponding trans regioadducts.Subsequent functional group manipulation under strict configurational control affords the isomericcis adducts. Chemoselective functionalization of the diamine moiety in 1,2-diaminoinositolderivatives can be achieved by the proper design of the reaction sequence and choice of reagents.The described protocols allow efficient access to each of the eight possible configurations of the1,2-diamino and 1,2-amino alcohol moieties from chemical modifications of the epoxide moiety onthe common precursor 9.
|