Überführung des Pregnandiols in Corpus‐luteum‐Hormon

Hormones

“…He transformed this into progesterone following a protocol from Butenandt. [26] In his search for a more productive source of pregnanediol, Marker discovered that bull's urine is very rich in this steroid [27], what made Parke-Davis & Co. consider to set up a large stable of bulls for the production of progesterone (Fig. 6.11).…”

Utilization of Common Natural Products as Synthons: Preparation of Progesterone from Lithocholic Acid

“…Crystallization of the crude material from Me2CO yielded 140 mg of 4-bromopregna-3,20-dione [10]: mp 172.5-173.6°[lit. (24) 185];…”

Chemical interrelationships in the cholane group

“…1It has now been agreed to name this hormone progesterone [Science, 82, 153 A confirmation of the correctness of the chemical constitution of this hormone has been afforded by partial synthesis of this principle, which has been brought about in two different ways. On oxidation, bromination, and renewed oxidation of pregnanediol (formula I) one obtains a product of the constitution indicated by formula K, and on removal of one molecule of HBr from the latter compound, a substance is obtained which is identical with the active principle (23). The same substance has also been obtained from stigmasterol, C29H48O (formula N), which is a phytosterol and closely related chemically to cholesterol (23,24).…”

“…On oxidation, bromination, and renewed oxidation of pregnanediol (formula I) one obtains a product of the constitution indicated by formula K, and on removal of one molecule of HBr from the latter compound, a substance is obtained which is identical with the active principle (23). The same substance has also been obtained from stigmasterol, C29H48O (formula N), which is a phytosterol and closely related chemically to cholesterol (23,24). These two syntheses prove that the corpus luteum hormone contains the same ring structure as is present in the sterols described in this review.…”