title: [1,2,3,4-13C] testosterone and [1,2,3,4-13C] estradiol.
abstract: The preparation of [1,2,3,4-13C] testosterone and of [1,2,3,4-13C] estradiol by total synthesis is described. The 13C labels are introduced by alkylating intermediate 1 with [1,2,3,4-13C]l-iodo-3,3-ethylenedioxybutane (2) to obtain intermediate 10. Hydrolysis of the ketal function, cyclization, aromatization and removal of protective groups gave [1,2,3,4-13C] estradiol. Labeled testosterone was prepared by methylating intermediate 10 and by subsequent treatment with acid. The labeled steroids can be used as tracers for in vivo metabolic studies and as internal standards for the development of definitive gc-ms quantitative methods.
mesh_terms: D002247:Carbon Isotopes; D055598:Chemical Phenomena; D002621:Chemistry; D004958:Estradiol / Q000138:chemical synthesis*; D013739:Testosterone / Q000138:chemical synthesis*
chemical_list: D002247:Carbon Isotopes; D013739:Testosterone; D004958:Estradiol