A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones: intermediates in the synthesis of 2(3H)-furanones.
A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-protected D-ribonolactone, 5-O-protected 2,3-dideoxy-D-glycero-pent-2-enono-1,4-lactones were synthesized and reacted with R2CuLi or a complex PhSCu(RMgBr)n to give respectively the 3-C-alkyl or 3-C-phenyl compounds. Details of the preparation of the O-protected intermediates, as well as the selection of the organometallic reagents, are provided.
Raveendranath
P C
PC
Department of Chemistry, University of Tennessee, Knoxville 37996-1600.
Blazis
V J
VJ
Agyei-Aye
K
K
Hebbler
A K
AK
Gentile
L N
LN
Hawkins
E S
ES
Johnson
S C
SC
Baker
D C
DC
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis; D009904:Optical Rotation; D012266:Ribose / Q000031:analogs & derivatives
D000900:Anti-Bacterial Agents; D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; D009705:Nucleosides; C057020:ribonolactone; D012266:Ribose; D015107:4-Butyrolactone