THE SYNTHESIS OF 17-(METHYL-C14)-TESTOSTERONE AND 21-C14-PROGESTERONE

The synthesis of 17-(methyl-C14)-testosterone and 21-C14-progesterone.

The use of steroid hormones containing tagged atoms promises to have an important part in the study of their metabolism. The relative availability of radioactive Cl4 manufactured in the uranium chain-reacting pile at Oak Ridge has facilitated the synthesis of such compounds containing labeled carbon atoms (1). Through the cooperation of Dr. Konrad Dobriner of the Sloan-Kettering Institute for C...

The conversion of testosterone-3-C14 to C14-estradiol-17beta by human ovarian tissue.

There is a considerable body of biological data linking testosterone and other 19-carbon steroids with the estrogens. Both ovaries and testes may, under certain circumstances, produce androgens and estrogens (14). The administration of testosterone and other androgens to human subjects leads to an increased urinary excretion of estrogenic material (5-lo), which has been identified as estrone, e...

The excretion of metabolites of progesterone-21-C14 after intragastric administration to rats.

Our interest in the relative inactivity of progesterone by oral administration reported by several investigators (14) has led us to utilize progesterone-21-Cl4 to ascertain whether the diminished activity could be related to absorption from the gastrointestinal tract. Since our experiments clearly showed that the metabolites were excreted more rapidly in urine than Grady et al. (5, 6) had obser...

The synthesis of 3,4-benzpyrene-5-C14 and of 2-acetylaminofluorene-9-C14.

Synthesis of D-Glucose-1-C14 and D-Mannose-1-C14

Heretofore, radiochemical yields of sugars position-labeled with carbon-14 have been only 5 to 10 percent. This paper reports an improved cyanohydrin synthesis, and the preparation of D-glucose-1-C and D-mannose-1-C from D-arabinose in yields of about 50 percent. Low yields in prior syntheses appear to have been due to several inefficient steps, and to the fact that extension of the carbon chai...