Untersuchungen in der Sexualhormon‐Reihe

Synthesis of 17α ‐ethynylestradiol‐6, 7‐3H and 17α‐ethynylestradiol‐6,7‐3H, 3‐cyclopentyl‐1‐14C ether

“…Inhoffe, et ul. (12) prepared I l k by allowing potassium acetylide to add to IIa in a mixture of dioxane and liquid ammonia. Despite the attractive yield of 90 % reported for this reaction, the small quantities of high specific activity steroids precluded the use of this procedure.…”

Nuclear Receptors as Drug Targets: A Historical Perspective of Modern Drug Discovery

“…Therefore the discovery of a compound with contraceptive properties and better drug-like properties was the focus of synthetic efforts with progesterone as a lead structure. Inhoffen had discovered already in 1938 that 17a-ethynyl-testosterone was a weakly active progestin when administered orally [29]. More than a decade later, in 1951 C. Djerassi and a team of scientists at Synthex succeeded in synthesizing 19-nor-17a-ethynyl-testosterone or norethindrone [30].…”

Hormones

“…The production of spironolactone from 17α-ethynylandrost-5-ene-3β,17β-diol (114) [238,239] involves the following steps (Searle) [240]:…”