Stereoselective synthesis of d-desosamine and related glycals via tungsten-catalyzed alkynol cycloisomerization.
Stereoselective synthesis of d-desosamine diacetate ester (iii, R = Ac) was achieved from the glycal (ii). generated by tungsten carbonyl-catalyzed cycloisomerization of the corresponding amino-alkynol (i). A wide variety of N-substituents (R, R') are compatible with the cycloisomerization, provided that at least one R or R' is an acyl derivative.
Davidson
Mary H
MH
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
McDonald
Frank E
FE
D000438:Alcohols / Q000737:chemistry*; D000606:Amino Sugars / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D014414:Tungsten / Q000737:chemistry*
D000438:Alcohols; D000606:Amino Sugars; C110125:desosamine; D014414:Tungsten