TY - JOUR T1 - Highly diastereoselective 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate: synthesis of polyhydroxylated perhydroazaazulenes JF - Synlett Y1 - 2009 A1 - Bande, Omprakash P. A1 - Jadhav, Vrushali H. A1 - Puranik, Vedavati G. A1 - Dhavale, Dilip D. KW - 1 KW - 3-dipolar nitrone olefin cycloaddition (DNOC) KW - diastereoselectivity KW - Iminosugars KW - inhibitors KW - nitrone AB -

An intermolecular 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate was found to be perfectly diastereoselective at the nitrone carbon to give exclusive formation of isoxazolidine. The N-O bond reductive cleavage in isoxazolidine followed by lactam reduction afforded a pyrrolidine ring skeleton with sugar appendage that on acetonide cleavage and reductive amino-cyclization gave hitherto unknown hydroxymethyl-substituted hexa- and pentahydroxy perhydroazaazulenes.

PB - GEORG THIEME VERLAG KG CY - RUDIGERSTR 14, D-70469 STUTTGART, GERMANY IS - 12 U3 - Foreign U4 - 2.447 ER -