Stereoselective synthesis of vancosamine and saccharosamine glycals via tungsten-catalyzed alkynol cycloisomerization.
[reaction: see text] A stereoselective synthesis of the C-3 branched amino glycals of vancosamine and saccharosamine is described that features a tungsten carbonyl catalyzed cycloisomerization of the corresponding alkynyl alcohol.
Cutchins
William W
WW
Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, Georgia 30322.
McDonald
Frank E
FE
D000480:Alkynes / Q000737:chemistry; D000606:Amino Sugars / Q000138:chemical synthesis; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003837:Deoxy Sugars / Q000138:chemical synthesis; D006595:Hexosamines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013395:Sucrose / Q000138:chemical synthesis*; D014414:Tungsten / Q000737:chemistry
D000480:Alkynes; D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D003837:Deoxy Sugars; D006595:Hexosamines; C001946:vancosamine; D013395:Sucrose; D014414:Tungsten