Synthesis of some steroid spin labels.
An improved synthesis of spin-labeled cortisol, cortisone, and testosterone using N,N'-cyclohexylcarbodiimide (DCC) is reported. The spin labeled steroids are shown to result from the esterification at the most reactive C(21) and C(17) hydroxyl groups. A mild and high yield oxidation of cortisol spin label to cortisone spin label by chromium trioxide-pyridine is also discussed.
D003348:Cortisone / Q000378:metabolism; D004024:Dicyclohexylcarbodiimide; D004578:Electron Spin Resonance Spectroscopy; D006854:Hydrocortisone / Q000378:metabolism*; D013113:Spin Labels / Q000138:chemical synthesis*; D013739:Testosterone / Q000378:metabolism; D014156:Transcortin / Q000378:metabolism*
D013113:Spin Labels; D013739:Testosterone; D004024:Dicyclohexylcarbodiimide; D014156:Transcortin; D003348:Cortisone; D006854:Hydrocortisone