S. Yokota, Mitsuru Nishida, O. Mitsunobu
Jun 1, 1983
Citations
0
Influential Citations
8
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Reaction of methyl 2,3-anhydro-4,6-dideoxy-α-D-ribo-hexopyranoside with MgI2 exclusively afforded methyl 3,4,6-trideoxy-3-iodo-α-D-xylo-hexopyranoside which was dehalogenated by treatment with LiAlH4 to give methyl 3,4,6-trideoxy-α-D-erythro-hexopyranoside (2). Hydrolysis of 2 and subsequent treatment with ethoxycarbonylmethylenetriphenylphosphorane gave ethyl (2E, 4R, 7R)-4,7-dihydroxy-2-octenoate (10). Oxidation of 10 by-active MnO2 resulted in the formation of an equilibrium mixture of ethyl (2E, 7R)-7-hydroxy-4-oxo-2-octenoate (the carbon skeleton of pyrenophorin) and cyclic hemiacetal. On treatment with acetic anhydride, the mixture afforde dethyl (2E, 7R)-7-acetoxy-4-oxo-2-octenoate.