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Journal
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Total synthesis of
deoxymannojirimycin and D-mannolactam via carbonylation of
5-vinyloxazolidin-2-ones.
Julian G. Knight and
Kirill Tchabanenko, Tetrahedron, 2003, 59, 281. |
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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. |
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