Synthesis of [11,11,12,12-2H4]progesterone for mass spectral investigations of peripheral metabolism

Steroids. 1990 May;55(5):222-7. doi: 10.1016/0039-128x(90)90019-8.

Abstract

Hecogenin has been transformed into [11,11,12,12-2H4]progesterone via base-catalyzed isotope exchange with D2O (at C-11), carbenic decomposition of the 12-tosylhydrazone formed by the use of [N,N,N'-2H3]toluene-p-sulfonylhydrazine, and reduction with [2H2]diimide to give [11,11,12,12-2H4]tigogenin, followed by standard degradation of the spiroketal side chain and dehydrogenation in ring A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Desoxycorticosterone / metabolism
  • Deuterium*
  • Isotope Labeling / methods*
  • Mass Spectrometry
  • Oxidation-Reduction
  • Progesterone / chemical synthesis*
  • Progesterone / metabolism

Substances

  • Desoxycorticosterone
  • Progesterone
  • Deuterium