Gewinnung von 1;4‐Bisdehydro‐3‐oxo‐steroiden. Über Steroide, 139. Mitteilung

Meystre, Ch.; Frey, H.; Voser, W.; Wettstein, A.

doi:10.1002/hlca.19560390314

Cited by 82 publications

(8 citation statements)

References 26 publications

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“…Many methods for introducing the 1,4-diene into the A-ring of steroids have been reported, for example, the use of selenium compounds, − DDQ (2,3-dichloro-5,6- dicyanobenzoquinone) as an oxidizing agent, , fermentation, − and bromination−dehydrobromination. − Among these, selenium compounds and DDQ are toxic and even gave the products in moderate yield. Fermentation needs a low substrate concentration and a very long reaction time, even though in the course of the production of corticosteroids, such as androstanedione and androstadienedione, from stigmasterol ( 6 ) and sitosterol ( 7 ), fermentation is the method for introducing alkenes into the A-ring.…”

Section: Introductionmentioning

confidence: 99%

Improved Synthetic Route to Dexamethasone Acetate from Tigogenin

Ohta

Zhang

Torihara

et al. 1997

Org. Process Res. Dev.

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In the synthesis of dexamethasone acetate from tigogenin, the introduction of the 17α-hydroxy-16α-methyl and the 1,4-diene moieties was improved. For the introduction of the 17α-hydroxy-16α-methyl moiety, the key step, epoxidation, was accomplished in high yield with peracetic acid in a buffer solution of sodium acetate and acetic acid (overall yield from 17-ene substrate to 17α-hydroxy-16α-methyl intermediate: 95.3%). Then the introduction of the 1,4-diene in the A-ring was greatly improved by bromination−dehydrobromination, in which dehydrobromination proceeded smoothly in a solvent system that was a mixture of DMF and 6% of water (82.6% isolated yield of 1,4-diene based on 3-oxo compound).

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Section: Introductionmentioning

confidence: 99%

Improved Synthetic Route to Dexamethasone Acetate from Tigogenin

Ohta

Zhang

Torihara

et al. 1997

Org. Process Res. Dev.

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“…(a) Preparation of 14oc-hydroxyandrosta-1,4diene-3,17-dione from 140c-hydroxyandrost-4-ene-3,17-dione. For the introduction of the double bond, the method of Meystre, Frey, Voser & Wettstein (1956) was used. A mixture of 14ochydroxyandrost-4-ene-3,17-dione (10g.…”

Section: Methodsmentioning

confidence: 99%

14α-Hydroxyoestrone, a new oestrogen metabolite

Knüppen¹,

Haupt²,

Breuer³

1967

Biochemical Journal

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1. Incubation of oestrone with ox adrenal glands leads to the formation of two main metabolites, one of which has recently been identified as 15alpha-hydroxyoestrone; the second metabolite (Oe-5) has now been obtained in crystalline form and identified as the hitherto unknown 14alpha-hydroxyoestrone. 2. The identity of compound Oe-5 with 14alpha-hydroxyoestrone was confirmed conclusively by comparison with 14alpha-hydroxyoestrone that was synthesized by pyrolytic aromatization of 14alpha-hydroxyandrosta-1,4-diene-3,17-dione. 3. The physical and chemical properties as well as the oestrogenic activity of 14alpha-hydroxyoestrone are described. 4. The biogenesis and metabolism of 14alpha-hydroxyoestrone were studied in various tissue preparations.

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“…Prednisone can be produced chemically by a process developed by the Schering Corporation from pregnane-17α,21-diol-3,11,20-trione 21-acetate (119) involving a 1,4-dibromide and subsequent hydrogen bromide elimination with pyridine [242]. Other methods use the 1,2-dehydrogenation of cortisone with selenium dioxide [243,244].…”

Section: 2-dehydrocorticosteroidsmentioning

confidence: 99%