Organocatalytic syn-aldol reactions of dioxanones with (S)-isoserinal hydrate: synthesis of L-deoxymannojirimycin and L-deoxyidonojirimycin.
We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2-methyl-1,3-dioxan-5-one. The key steps include diastereoselective proline-catalyzed syn aldol transformation and a reductive amination/cyclization.
Palyam
Nagarjuna
N
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
Majewski
Marek
M
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D004146:Dioxanes / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D011392:Proline / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives / Q000737:chemistry
D000447:Aldehydes; D000588:Amines; D000998:Antiviral Agents; D004146:Dioxanes; D004791:Enzyme Inhibitors; C542750:L-deoxyidonojirimycin; D017485:1-Deoxynojirimycin; D012694:Serine; C072421:isoserine; C116609:3-hydroxybutanal; D011392:Proline