Pc. Raveendranath et al., 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, Carbohydrate research, 253, 1994, pp. 207-223
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 modif
ied nucleosides and antibiotic sugars, were synthesized from D-ribonol
actone. 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 synt
hesized and reacted with R(2)CuLi or a complex PhSCu(RMgBr)(n) to give
respectively the 3-C-alkyl or 3-C-phenyl compounds. Details of the pr
eparation of the O-protected intermediates, as well as the selection o
f the organometallic reagents, are provided.