Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide

12 pages, 8 schemes, 1 table.-- PMID: 16277302 [PubMed].-- Printed version published Mar 15, 2005.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo050521aA 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.Financial support from Ministerio de Ciencia y Tecnología (Spain), Project BQU2002-03737, and DURSI (Generalitat de Catalunya), Projects 2001SGR00085 and 2001SGR00342.Peer reviewe