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Título

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

AutorSerrano, Pedro; Llebaria, Amadeu; Delgado Cirilo, Antonio
Palabras claveRegio- and stereoselective synthesis
Aminoinositols
N-octanoyl
Conduritol B epoxide
Fecha de publicación7-sep-2005
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 70(20): 7829–7840 (2005)
ResumenA 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.
Descripción12 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/jo050521a
Versión del editorhttp://dx.doi.org/10.1021/jo050521a
URIhttp://hdl.handle.net/10261/15657
DOI10.1021/jo050521a
ISSN0022-3263 (Print)
1520-6904 (Online)
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