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Título: | Regio- and stereoselective synthesis of aminoinositols and 1,2-diaminoinositols from conduritol B epoxide |
Autor: | Serrano, Pedro; Llebaria, Amadeu CSIC ORCID; Delgado Cirilo, Antonio CSIC ORCID | Palabras clave: | Regio- and stereoselective synthesis Aminoinositols N-octanoyl Conduritol B epoxide |
Fecha de publicación: | 7-sep-2005 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 70(20): 7829–7840 (2005) | Resumen: | 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. | Descripción: | 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/jo050521a | Versión del editor: | http://dx.doi.org/10.1021/jo050521a | URI: | http://hdl.handle.net/10261/15657 | DOI: | 10.1021/jo050521a | ISSN: | 0022-3263 | E-ISSN: | 1520-6904 |
Aparece en las colecciones: | (IQAC) Artículos |
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