Über Steroide und Sexualhormone. 170. Mitteilung. Synthese von 14‐Allo‐17‐iso‐desoxy‐corticosteron‐acetat

Heußer, H.; Frick, Nelly; Plattner, Pl. A.

doi:10.1002/hlca.19500330519

Cited by 5 publications

(3 citation statements)

References 16 publications

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“…Bachmann & Ramirez (36) have prepared dl-16-aza-desoxyisoequilenin and dl-16-aza-desoxyequilenin and have also obtained evidence in favor of a trans CID ring juncture for the normal steroids. Heusser et al (37,38) have synthesized 14-allo-17-iso desoxycorticosterone acetate (no biological activity reported) and 14-allo-17-epi-testosterone (no androgenic activity). In the Corner-Allen test 14-allo-17-iso-progesterone is inactive in 10 mg. doses, but in the capon test, is from!…”

Section: Partial Synthesis Of Steroidsmentioning

confidence: 99%

Biochemistry of Steroids

Lieberman¹,

Dobriner²

1951

Annu. Rev. Biochem.

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The unique role of the steroid hormones in nearly all phases of life has been established. With the discovery of the sex hormones in the early thirties, it seemed that the physiological action of steroids was primarily concerned with the phenomena of sex. With ' the discovery of the steroid hormones of the adrenal gland in the late thirties it was soon found that these compounds had a profound influence on metabolism and that this was also true of the so-called sex hormones. Progress in a steadily expanding area of investiga tion in biology, biochemistry, and medicine was handicapped by the lack of sufficient quantities of the adrenal hormones. These hormones were for all practical purposes not available because the chemical introduction of the biologically essentially C-ll oxygen function into the steroid nucleus had not been accomplished. As a result of the brilliant work of Reichstein, Kendall, Gallagher, and Wintersteiner in the middle forties, this objective was achieved and together with the further contributions· of these investiga tors, as well as the very significant achievements of Sarett, Miescher, Wallis, and Julian, the large scale preparation of the most important cortical hor mones became practicable. Fin ally, large amounts were made available for extensive investigations. At about the same time the adrenfll-stimulating hormone of the pituitary (ACTH) became available in sufficient amounts and in a usable stage of purity so that both hormones were at hand for the study of the essential physiological processes controlled by the internal secre tions of the adrenal. Within an extremely short time the epoch-making dis covery of Hench and Kendall of the effect of these hormones in arthritis was reported. These observations opened a new era in medicine, physiology and biochemistry, and it was recognized as such by the award of the Nobel prize to Reichstein, Kendall, and Hench in 1950. The number of investigations has increased rapidly during the last 1 The following abbreviations have been used in this review. It should be noted that, unless otherwise mentioned, reference has been made to the acetoxy derivatives of the adrenal hormones

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Section: Partial Synthesis Of Steroidsmentioning

confidence: 99%

Biochemistry of Steroids

Lieberman¹,

Dobriner²

1951

Annu. Rev. Biochem.

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“…The conversion of the readily available cardiac aglycone strophanthidin into analogs of steroid hormones having oxygen at position 19 has been one of the objectives of work being performed in this laboratory (cf. e.g.…”

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confidence: 99%

“…""1 was ascribed to contamination with some impurity. 19-Acetoxyprogesterone (XI) was measured in both chloroform and carbon disulfide solution. In chloroform there were bands at 1737 cm.…”

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confidence: 99%

INVESTIGATIONS ON STEROIDS. XXIV. 19-HYDROXY-11-DESOXYCORTICOSTERONE AND 19-HYDROXYPROGESTERONE^*1

Barber¹,

Ehrenstein²

1954

J. Org. Chem.

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1. 19-Acetoxy-3-oxo-A4-etienic acid (I), obtainable by degradation of strophanthidin (6), has been converted by way of the diazoketone (II) into 19hydroxy-11 -desoxycorticosterone (IX) and 19-hydroxyprogesterone (X) respectively. The 19-monoacetate (VI), the 21-monoacetate (VIII), and the 19,21-diacetate (V) of IX have been described. X was characterized by the acetate (XI).2. The bioassays of 19-hydroxy-11 -desoxycorticosterone (IX) and of 19hydroxyprogesterone (X) are reported.3. The preparations of 19-hydroxy-3-oxo-A4-etienamide (IV) and of 3-oxo-A4-etienamide are discussed.Philadelphia 4, Pennsylvania

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Steroide und Sexualhormone. 171. Mitteilung. Über eine neue Synthese von Δ^5,17,20‐3‐β‐Acetoxy‐pregnadien

Fischer

Lardelli

Jeger

1950

Helvetica Chimica Acta

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Bei der Reduktion von tl, /I-ungesSlttigten Carbonyl-Verbindungen nach Wolff -Kish.ner kann gleichzeitig rnit der Reduktion der Carbonylgruppe eine Verschiebung der Doppelbindung stattfinden2). Die Verschiebung der Doppelbindung ist zuerst beim Erhitzen der tl, /I-ungesattigten Carbonyl-Verbindungen rnit Hydrazinhydrat und Natriumathylat festgestellt worden, findet aber, wie wir nun gefunden haben, auch bei der Behandlung ihrer Semicarbazone mit Natriumathylat statt. Als ein besonders interessantes Beispiel der letzten Reduktionsvariante, die in gewissen Fallen dem Erhitzen der freien Carbonyl-Verbindungen rnit Hydrazinhydrat und Natriumathylat, vorzuziehen ist, beschreiben wir in dieser Arbeit die Uberfiihrung von A 5 ; 16-3/I-0xgpregnadien-20-on (1)3)4) in das A 5 ; 17~20-3/I-Acetoxy-pregnadien (V)5).Durch Umsetzung von A 5 ; 16-3/I-Acetoxy-pregnadien-20-on (11) rnit Semimrbazid-acetat in methanolischer Losung gewmnen wir zuerst das amorphe, jedoch analysenreine Semicsrbazon 111. Beim Erhitzen rnit 2-proz. Natriumathylat-Losung auf 300° ging I11 in die in reiner Form nicht isolierte Verbindung IV iiber, welche bei der Acetylierung rnit Acetanhydrid-Pyridin bei Zimmertemperatur das bekannte A 5 ; lT? 20-3/?-Acetoxy-pregnadien (V) lieferte. Das auf dieseni Wege gewonnene Praparat von V zeigte sich nach Schmelzpunkt, Mischprobe und spez. Drehung rnit einem friiher von L. Rua.icka, W . Goldberg & E. Hardeggerj) durch Reduktion von d5-38,17&Dioxy-17a-at.hinyl-mdrosten (VI) rnit Natrium und Athylalkohol hergestellten Prapamt von V als ident'isch. Auch die 1R.-Absorptions-spektren6) bcider Proben (Figur A, Kurve 1 und 2 ) waren identisch. l) 170. Mitt. Helv. 33, 1260 (1950). Gleichzeitig 2. Mitt. in der Reihe: Uber die Reduktion von a, 8-nngesnttigten Carbonylverbindungen nach Wolf/-Kishner; 1. Mitt.

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Über Steroide und Sexualhormone. 170. Mitteilung. Synthese von 14‐Allo‐17‐iso‐desoxy‐corticosteron‐acetat

Cited by 5 publications

References 16 publications

Biochemistry of Steroids

Biochemistry of Steroids

INVESTIGATIONS ON STEROIDS. XXIV. 19-HYDROXY-11-DESOXYCORTICOSTERONE AND 19-HYDROXYPROGESTERONE^*1

Steroide und Sexualhormone. 171. Mitteilung. Über eine neue Synthese von Δ^5,17,20‐3‐β‐Acetoxy‐pregnadien

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Über Steroide und Sexualhormone. 170. Mitteilung. Synthese von 14‐Allo‐17‐iso‐desoxy‐corticosteron‐acetat

Cited by 5 publications

References 16 publications

Biochemistry of Steroids

Biochemistry of Steroids

INVESTIGATIONS ON STEROIDS. XXIV. 19-HYDROXY-11-DESOXYCORTICOSTERONE AND 19-HYDROXYPROGESTERONE*1

Steroide und Sexualhormone. 171. Mitteilung. Über eine neue Synthese von Δ5,17,20‐3‐β‐Acetoxy‐pregnadien

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INVESTIGATIONS ON STEROIDS. XXIV. 19-HYDROXY-11-DESOXYCORTICOSTERONE AND 19-HYDROXYPROGESTERONE^*1

Steroide und Sexualhormone. 171. Mitteilung. Über eine neue Synthese von Δ^5,17,20‐3‐β‐Acetoxy‐pregnadien