01479nas a2200241   4500008004100000022001400041245016200055210006900217260007500286300001400361520051000375653000600885653005000891653002500941653001600966653001500982653001200997100002501009700002501034700002601059700002301085856012901108       2009                        eng d  a0936-521400aHighly diastereoselective 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate: synthesis of polyhydroxylated perhydroazaazulenes0 aHighly diastereoselective 13dipolar cycloaddition of a Dgalactos  aRUDIGERSTR 14, D-70469 STUTTGART, GERMANYbGEORG THIEME VERLAG KGcJUL  a1959-19633 a<p>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.</p>10a110a3-dipolar nitrone olefin cycloaddition (DNOC)10adiastereoselectivity10aIminosugars10ainhibitors10anitrone1 aBande, Omprakash, P.1 aJadhav, Vrushali, H.1 aPuranik, Vedavati, G.1 aDhavale, Dilip, D.  uhttps://library.ncl.res.in/content/highly-diastereoselective-13-dipolar-cycloaddition-d-galactose-derived-nitrone-dimethyl-0