Bromination of Certain Ketosteroids and a Partial Synthesis of Œstradiol, Œstrone and Equilenin

Rosenkranz, G.; Djerassi, Carl; Kaufmann, St.; Pataki, J.; Romo, Juan Antonio

doi:10.1038/165814b0

Cited by 6 publications

(2 citation statements)

References 3 publications

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“…Dehydrohalogenation with coIlidine afforded ,6,1.4-androsta diene-3, 17 -dione which was aromatized to estrone in 15 to 20 per cent yield. Rosenkranz, Djerassi et al (13,14,15) reached this goal by th� series of reactions outlined in Figure 1. Thus it is now possible to prepare 6-dehy dro-estrone, estrone, equilenin, or their corresponding 17 -hydroxy deriva tives in good yield from either testosterone, �f-androstene-3,17-dione or �1.4-androstadiene-3, 17-dione.…”

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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“…1) at 228, 266, and 304 m#i, and on methylation to the methyl ether Vc. The phenol V thus exhibited the typical negative rotation of 6-dehydrophenols (6) and the characteristic ultraviolet absorption spectrum of a phenol with an additional double bond in the meta position (3,4,7). Catalytic hydrogenation of the acetate Vb and saponification produced l-methyl-3-hydroxy-19-nor-l ,3,5cholestatriene (Ha) with m.p.…”

mentioning

confidence: 99%

Steroids. Ix. The Dienone-Phenol Rearrangement in the Cholesterol Series

Romo¹,

Djerassi²,

Rosenkranz³

1950

J. Org. Chem.

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Microbial hydrolysis of 17 β-acetoxy steroidal compounds during aromatization by Arthrobacter simplex

Zhou

Yuan

1983

Acta Chim. Sin.

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Steroidal compounds containing 17β‐acetoxy group after aromatization by Arthrobacter simplex afforded 17β‐hydroxy‐, 17‐keto‐ or unhydrolyzed 17β‐acetoxy‐ring A‐aromatic compounds. 17‐Keto‐compounds were probably formed through the oxidation of the corresponding 17 β‐hydroxyl group during fermentation with this microorganism. Hydrolysis of 17 β‐acetoxy group is dependent upon other substituents present in the substrates.

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Bromination of Certain Ketosteroids and a Partial Synthesis of Œstradiol, Œstrone and Equilenin

Cited by 6 publications

References 3 publications

Biochemistry of Steroids

Biochemistry of Steroids

Steroids. Ix. The Dienone-Phenol Rearrangement in the Cholesterol Series

Microbial hydrolysis of 17 β-acetoxy steroidal compounds during aromatization by Arthrobacter simplex

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