ePrints

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

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

Downloads

Full text for this publication is not currently held within this repository. Alternative links are provided below where available.

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

Altmetrics

Share