Total synthesis of deoxymannojirimycin and d-mannolactam via carbonylation of 5-vinyloxazolidin-2-ones |
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| Authors: | Julian G Knight Kirill Tchabanenko |
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| Institution: | School of Natural Sciences, Newcastle University, Bedson Building, Newcastle upon Tyne NE1 7RU, UK |
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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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| Keywords: | deoxymannojirimycin carbonylation d-mannolactam" target="_blank">d-mannolactam |
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