A synthesis of L-vancosamine derivatives from non-carbohydrate precursors by a short sequence based on the Marshall, McDonald, and Du Bois reactions.
[reaction: see text] The carbamate-protected l-vancosamine glycal, viewed as a universal precursor for vancosamine derivatives, was prepared by a short scheme based on diastereoselective addition of an allenyl stannane to a lactaldehyde ether, the tungsten-catalyzed alkynol cycloisomerization, and the rhodium-catalyzed C-H insertion of a carbamate nitrogen. This sequence is a prototype for a new and efficient strategy for the synthesis of 3-amino sugar derivatives. The key intermediate was elaborated to the silyl ether of N,N-dimethyl vancosamine glycal.
Parker
Kathlyn A
KA
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA. kparker@notes.cc.sunysb.edu
Chang
Wonsuk
W
D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006595:Hexosamines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D006595:Hexosamines; D007202:Indicators and Reagents; C001946:vancosamine