Synthesis of [11,11,12,12-2H4]progesterone for mass spectral investigations of peripheral metabolism.
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.
Kirk
D N
DN
Department of Chemistry, Queen Mary College, London, UK.
Smith
C Z
CZ
Honour
J W
JW
D003900:Desoxycorticosterone / Q000378:metabolism; D003903:Deuterium; D007553:Isotope Labeling / Q000379:methods*; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D011374:Progesterone / Q000138:chemical synthesis* / Q000378:metabolism
D003900:Desoxycorticosterone; D011374:Progesterone; D003903:Deuterium