Synthesis of d-pilocarpine-N-14CH3.
The total synthesis of d-pilocarpine specifically labeled as N-14CH3 is reported. dl-Homopilopic acid was prepared as a key intermediate and resolved into the d-enantiomer via the alpha-methylbenzylamine salt. The penultimate intermediate, 2-mercaptopilocarpine, was desulfurized by oxidation with dilute hydrogen peroxide, minimizing isomerization to isopilocarpine. Procedures for the analysis of pilocarpine-isopilocarpine mixtures by high-pressure liquid chromatography are also described.
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007536:Isomerism; D008722:Methods; D010862:Pilocarpine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis
D013438:Sulfhydryl Compounds; D010862:Pilocarpine; C011270:homopilopic acid; D015107:4-Butyrolactone