Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide.
[Chemical reaction: See text] 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 analogue 22, respectively, is described. In all cases, the synthetic methodologies rely on the regio- and stereocontrolled azidolysis of the starting precursors to give the corresponding trans regioadducts. Subsequent functional group manipulation under strict configurational control affords the isomeric cis adducts. Chemoselective functionalization of the diamine moiety in 1,2-diaminoinositol derivatives 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 the 1,2-diamino and 1,2-amino alcohol moieties from chemical modifications of the epoxide moiety on the common precursor 9.
Serrano
Pedro
P
Unidad de Química Farmacéutica (Unidad Asociada al CSIC), Facultad de Farmacia, Universidad de Barcelona, Avda. Juan XXIII, s/n, 08028 Barcelona, Spain.
Llebaria
Amadeu
A
Delgado
Antonio
A
D000588:Amines; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013237:Stereoisomerism
D000588:Amines; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007294:Inositol; C011423:conduritol epoxide