POTENTIAL INHIBITORS OF HMG-COA REDUCTASE .2. SYNTHESIS OF 7-(2,4-DICHLOROPHENYL)-D-ERYTHRO-3-HYDROXY-5-HEPTANOLIDE, 6-(2,4-DICHLOROPHENYL)-D-ERYTHRO-2,4-DIHYDROXYHEXANE-1-SULFONIC ACID, AND 6-(2,4-DICHLOROPHENYL)-D-ERYTHRO-2,4-DIHYDROXYHEXYLPHOSPHONIC ACID

6-(2,4-Dichlorophenyl)-D-erythro-1,2,4-hexanetriol, synthesised from D-glucose, was partially silylated, then reacted with 2-methoxypropene to afford 1-O-tert-butyldimethylsilyl-6-(2,4-dichlorophenyl)-2,4-O-isopropylidene-D-erythro-1,2,4-hexanetriol (17). Desilylation of 17 gave 6-(2,4-dichlorophenyl)-2,4-O-isopropylidene-D-erythro-1,2,4-hexanetriol, which was converted into the 1-tosylate 18 and the 1-bromo derivative 19. Reaction of 18 with potassium thiolbenzoate gave, after debenzoylation, oxidation, and deprotection, 6-(2,4-dichlorophenyl)-D-erythro-2,4-dihydroxyhexane-1-sulfonic acid (4). Reaction of 18 or 19 with triethyl phosphite gave, after deprotection, 6-(2,4-dichlorophenyl)-D-erythro-2,4-dihydroxyhexylphosphonic acid (5), and reaction of 19 with potassium cyanide gave, after subsequent hydrolysis and deprotection, 7-(2,4-dichlorophenyl)-D-erythro-3-hydroxy-5-heptanolide (3).