Tetrahedron

Total synthesis of deoxymannojirimycin and D-mannolactam via carbonylation of 5-vinyloxazolidin-2-ones

JG Knight, K Tchabanenko

Index: Knight, Julian G.; Tchabanenko, Kirill Tetrahedron, 2003 , vol. 59, # 3 p. 281 - 286

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Citation Number: 45

Abstract

The stereoselective synthesis of piperidine alkaloids deoxymannojirimycin and d- mannolactam from d-serine has been achieved. The key step involves palladium-catalysed decarboxylative carbonylation of a serine-derived 5-vinyloxazolidin-2-one to give 6-(tert- butyldimethylsilyloxymethyl)-3, 6-dihydro-1H-pyridin-2-one which was subsequently converted into the title compounds.

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