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

Romo, J.; Djerassi, Carl; Rosenkranz, G.

doi:10.1021/jo01150a030

Cited by 15 publications

(8 citation statements)

References 5 publications

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“…Djerassi et al (18,19) have continued their studies of the dienone-phenol rearrangement in the steroid series. They have shown (19) that A l,4,6,_ androstatrien-17 -01-3-one rearranges to 1-methyl-.t.6-dehydro-estradiol which on hydrogenation yields 1-methyl-estradiol, and on dehydrogenation yields i-methyl-equilenin.…”

Section: Partial Synthesis Of Steroidsmentioning

confidence: 99%

“…They have shown (19) that A l,4,6,_ androstatrien-17 -01-3-one rearranges to 1-methyl-.t.6-dehydro-estradiol which on hydrogenation yields 1-methyl-estradiol, and on dehydrogenation yields i-methyl-equilenin. Their results, together with those of Woodward & Singh (20), demonstrate that the rearrangement products of .t.1,4-dien-3-one are not the expected i-methyl phenols but are still undefined compounds EquI' cnin "X-methyl hetero phenols."…”

Section: Partial Synthesis Of Steroidsmentioning

confidence: 99%

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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%

Section: Partial Synthesis Of Steroidsmentioning

confidence: 99%

Biochemistry of Steroids

Lieberman¹,

Dobriner²

1951

Annu. Rev. Biochem.

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“…Dibromination of the equilibrated material in the presence of hydrogen bromide gave 2a,4a-dibromo-5a-cholestan-3-one, which was dehydrobrominated with calcium carbonate in dimethylformamide to give cholesta-1,4-dien-3-one; further dehydrogenation with 2,3-dichloro-5,6-dicyanobenzoquinone gave the 1,4,6-trienone, which was subjected to the dienone-phenol rearrangement (Romo, Djerassi & Rosenkranz, 1950) to give 1-methylcholesta-1,3,5(10),6-tetraen-3-ol.…”

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confidence: 99%

The stereospecificity of tritium distribution in [1-3H]- and [1,2-3H2]-cholesterol and -cholecalciferol

Bell¹,

Kodíček²

1970

Biochemical Journal

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“…In point of fact, that was the accomplished scheme except that the initial exchange could be done only with acetic acid-0D71 on the diacetate of 67. Exchange of kryptogenin with strong base {e.g., NaOH) gives fesogenin (73)4 and with hydrochloric acid in methanol, bethogenin (74).4…”

mentioning

confidence: 99%