Herchel Smith

Biological effects of racemic and resolved 13β-ethyl-4-gonen-3-ones

Abstract Various biological effects of (±)-13β-ethyl-17β-hydroxygon-4-en-3-one, (±)-13β-ethyl-17α-ethynyl-17β-hydroxygon-4-en-3-one, and (±)-13β, 17α-diethyl-17β-hydroxygon-4-en-3-one were compared with resolved samples of the component enantiomers. The data were commensurate with the hypothesis that biological activity resides in the enantiomers possessing absolute configurations corresponding to those of the natural steroid hormones.

The identification of some human metabolites of norgestrel a new progestational agent.

n Norgestrel 1 (racemic 13-beta-ethyl-17-alpha-hydroxygon-4-en-3-one) a progestational agent with an angular ethyl group between Rings C and D, was studied by mass spectrometry to discover its structural characteristics. Synthesis of postulated metabolites of Norgestrel 1 for use in identification is described and structural formulas are given. Urine was used as a source to characterize fractions via mass spectra, and the fraction spectra are listed. The major metabolite was 13-beta-ethyl-17-alpha-ethynl-5-beta-gonan-3-alpha-1m-beta-diol 8c.n

Totally synthetic steroid hormones. Part XIV. (±)-18-methyl-19-norprogesterone, 18-methyl-19-nordesoxycorticosterone and related compounds

Abstract An account is given of the total synthesis of (±)-18-methyl-19-norprogesterone III, its 17α-epimer IIIa, (±)-18-methyl-19-nordesoxycorticosterone XIIa, its acetate XII, (±)-21-hemisuccinoyloxy-18-methyl-19-nor-5β-pregnan-3-one XIXb, and various cognate compounds. Also reported are the progestational activities of III and IIIa, the mineralocortiod activities of XII and XIIa, and some central nervous system effects of the sodium salt of XIXb.