合成路线1

A synthesis of [14C]-labeled cerivastatin has been developed: The decarboxylative bromination of 4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridine-3-carboxylic acid (I) gave the bromopyridine (II), which is treated with BuLi and [14C]-labeled CO2 affording the labeled carboxylic acid (III). The methylation of (III) with diazomethane gave the corresponding methyl ester (IV), which was reduced with LiAlH4 in ether to the alcohol (V). The reaction of (V) with SOCl2 afforded the chloromethyl derivative (VI), which was condensed with triethyl phosphite at 180 C to give the phosphonate (VII). The condensation of (VII) with the tetrahydropyran-2-carbaldehyde (VIII) by means of LDA in THF yielded the olefine (IX), which was treated with HCl in aqueous THF eliminating the protecting groups and thus, providing the epimeric mixture of hemiacetals (X). The oxidation of (X) with silver carbonate in refluxing toluene gave the lactone (XI), which was finally treated with NaOH in water/acetonitrile.