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Paper | Special issue | Vol 74, No. 1, 2007, pp.533-543
Published online, 4th December, 2007
DOI: 10.3987/COM-07-S(W)31
Reactions of Glycosan-Annelated Oxolactams

Swantje Thiering, Joachim Thiem,* and Jürgen Kopf

*Institute of Organic Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany

Abstract

Starting with 4-imido-mannosan and 2-imido-galactosan derivatives Norrish-Yang cyclization led to saccharide-annelated azepanediones and azocanediones. Following N-protection these lactams could be opened to give higher branched-chain carbohydrate components of the 4-amino-3-dehydro type. In some cases concomitant rearrangement reactions were observed to give α,β-unsaturated hydroxy lactams as well as saccharides linked to substituted furans.