Synthesis of multi-labeled cortisols and cortisones with 2H and 13C for study of cortisol metabolism in humans

A method is described for the preparation of multi-labeled cortisol and cortisone with C-13 and H-2 via the indan synthon method, starting from chiral 11-oxoindanylpropionic acid. [1,3-C-13(2)]Acetone was used for the syntheses of [1,2,4,19-C-13(4)]cortisol (cortisol-C-13(4)) and [1,2,4,19-C-13(4)]cortisone (cortisone-C-13(4)), and [1,3-C-13(2),1,1,1,3,3,3-H-2(6)]acetone was for [1,2,4,19-C-13(4),1,1,19,19,19-H-2(5)]cortisol (cortisol-C-13(4), H-2(5)) and [1,2,4,19-C-13(4),1,1,19,19,19-H-2(5)]cortisone (cortisone-C-13(4), H-2(5)). The chemical shifts for the C-13 and H-1 NMR spectra of cortisol and cortisone were fully assigned. (C) 2000 Elsevier Science Inc. All rights reserved.