[1,2,3,4-13C] testosterone and [1,2,3,4-13C] estradiol

Article abstract of DOI:10.1016/S0039-128X(84)80021-5

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.