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 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.