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