Highly diastereoselective 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate: synthesis of polyhydroxylated perhydroazaazulenes

TitleHighly diastereoselective 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate: synthesis of polyhydroxylated perhydroazaazulenes
Publication TypeJournal Article
Year of Publication2009
AuthorsBande, OP, Jadhav, VH, Puranik, VG, Dhavale, DD
JournalSynlett
Issue12
Pagination1959-1963
Date PublishedJUL
ISSN0936-5214
Keywords1, 3-dipolar nitrone olefin cycloaddition (DNOC), diastereoselectivity, Iminosugars, inhibitors, nitrone
Abstract

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.

DOI10.1055/s-0029-1217541
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.447

Divison category: 
Center for Material Characterization (CMC)