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

Lookup NU author(s): Dr Julian Knight, Dr Kirill Tchabanenko

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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. © 2003 Elsevier Science Ltd. All rights reserved.

Publication metadata

Author(s): Knight JG, Tchabanenko K

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2003

Volume: 59

Issue: 3

Pages: 281-286

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/S0040-4020(02)01534-X

DOI: 10.1016/S0040-4020(02)01534-X

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