THE SYNTHESIS OF PROGESTERONE-21-C¹⁴

Abstract

As a part of a program to study the intermediary metabolism of steroids, radioprogesterone (II) has been prepared. This labeled hormone was made by the alkylation of 3-keto-4-etiocholenoyl chloride with radioactive dimethylcadmium.

Ab → Abc → Abcd

“…In addition to brevity, it led to A 14 -16-ketosteroids which permitted the introduction of a variety of 17-substituents [35,36]. The method was also extended to the total synthesis of deoxycorticosterone [37], progesterone [38], and other nonaromatic steroids via methyl 3-ketoetiocholanate [39,40].…”

The Synthesis of 17α-Ethynyltestosterone-20,21--C14

“…The trap was removed from the train and attached to the manifold and the whole system was evacuated to 0.75 µ. The reaction flask was then shut off and the radioacetylene allowed to expand into the manifold 1 Obtained from Tracerlab, 55 Oliver St., Boston 10, Mass. The sample contained about 1 millicurie of Cu; however, according to instructions received with the sample and previous correspondence, only about two thirds of the radiocarbon can be recovered as radioacetylene.…”

“…The introduction of radiocarbon in the ethynyl group of this synthetic hormone provides a labeled compound for biological investigations such as its possible conversion to progesterone. The synthesis (1) and a metabolic study (2) of radioprogesterone has been previously reported from this laboratory. 'dil.…”

The Chemistry and Metabolism of the Steroid Hormones

“…Since preg nanediol administration itself leads to only slightly higher percentage recov eries (57) the implication of further degradation of pregnanediol is clear. Hope for more detailed analyses of progesterone metabolism is given by the preparation of 21-CU-progesterOll e having adequate specific activity for tracer studies (61,62), but ring-labeled progesterone would be highly de sirable, especially if side-chain scission occurs in the body.…”