Practical synthesis of optically pure 3,4-epoxy-5-methyldihydro-2(3H)-furanones from D-xylose by regio- and stereo-selective functionalization

Article abstract of DOI:10.1016/S0008-6215(00)90532-9

The known 1,2-O-isopropylidene-5-O-p-tolylsulfonyl-α-D-xylofuranose was converted into its 3-p-nitrobenzoate (13a) and 3-methanesulfonate (13b). (-)-(3S,4S,5R)-3,4-Epoxy-5-methyldihydro-2(3H)-furanone <(-)-8> was synthesized from 13a in 5 steps by convers