AN EFFICIENT SYNTHESIS OF Y-NUCLEOSIDE (WYOSINE) BY REGIOSPECIFIC METHYLATION OF N4-DESMETHYLWYOSINE USING ORGANOZINC REAGENT

Article abstract of DOI:10.1016/S0040-4039(00)95491-1

The reaction of the organozinc reagent, produced by the reaction of CH2I2 + Zn(C2H5)2 + glyme in diethylether at 20 deg C, regioselectively methylates the N⁴-nitrogen of N⁴-desmethylwyosine-triacetate 3 to give pure wyosine-triacetate 1e in 76percent isolated yield; no trace of the isomeric N⁵ methylated product is found in the latter reaction.Synthesis of a new congener of Y-nucleoside 1f is also reported for the first time from compound 5 in a high overall yield using a similar procedure.