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Summary The synthesis of a representative (9-fluoro-18-methyl-prednisolone) of the new class of 18-methylcorticosteroids is described.
Über Steroide 227. Mitteilung; 226. Mitt. vgl. 相似文献
Über Steroide 227. Mitteilung; 226. Mitt. vgl. 相似文献
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K. Heusler J. Kalvoda Ch. Meystre H. Ueberwasser P. Wieland G. Anner A. Wettstein 《Cellular and molecular life sciences : CMLS》1962,18(10):464-466
Summary The new methods for the production of 19-norsteroids described involve the conversion of 5-halogen-6-hydroxy-steroids into the corresponding 5-halogen-6:19-ethers either with lead tetraacetate or by the hypoiodite reaction8,10. The 6:19-oxygen bridge is then opened reductively either directly or after oxidation of the 6:19-ethers to lactones or preferably after introduction of a 4,6-3-oxo grouping. Acylolytic cleavage of the 4-3-oxo-6:19-ethers followed by alkaline hydrolysis gives 4,6-3-oxo-19-hydroxy-steroids. The 19-hydroxycompounds formed are easily converted into 19-norsteroids by known methods.
Über Steroide, 189. (vorläufige) Mitteilung; 188. Mitt. vgl.J. Kalvoda, J. Schmidlin, G. Anner undA. Wettstein, Exper.18, 398 (1962). 相似文献
Über Steroide, 189. (vorläufige) Mitteilung; 188. Mitt. vgl.J. Kalvoda, J. Schmidlin, G. Anner undA. Wettstein, Exper.18, 398 (1962). 相似文献
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Meystre Ch. Heusler K. Kalvoda J. Wieland P. Anner G. Wettstein A. 《Cellular and molecular life sciences : CMLS》1961,17(10):475-480
Summary The intramolecular substitution of the angular methyl groups in steroids by attack of O-radicals derived from 6-, 11, and 20-alcohols is discussed. Irrespective of their genesis, these radicals abstract a hydrogen atom from one of the said methyl groups, suitably oriented in-position. The C-radicals thus formed give different products depending on the neighbouring groups.It is shown that 20-hydroxy-18-C-radicals combine with iodine atoms, to give 18-iodides which can befurther substituted through radicals to give potential 18-oxo-compounds in high yield. In the case of 20-cyanohydrines, the intramolecular reaction of the 18-C-radical with the cyano groups gives rise to the new 18-cyano-20-oxo-steroids.With 6- and 11-O-radicalssingle substitution in 19-position predominates, since the steric arrangement of the primary product favours the intramolecular ether formation over a second substitution reaction.A general reaction scheme for these transformations is proposed.
Vorgetragen vonCh. Meystre am 23. 9. 61 anlässlich der Sommerversammlung der Schweiz. Chem. Gesellschaft in Biel (vgl. Chimia15, (1961), im Druck).
Über Steroide 180. Mitteilung. 179. Mitt. vgl.A. Wettstein, Exper.17, 329 (1961). 相似文献
Vorgetragen vonCh. Meystre am 23. 9. 61 anlässlich der Sommerversammlung der Schweiz. Chem. Gesellschaft in Biel (vgl. Chimia15, (1961), im Druck).
Über Steroide 180. Mitteilung. 179. Mitt. vgl.A. Wettstein, Exper.17, 329 (1961). 相似文献
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K. Heusler J. Kalvoda Ch. Meystre P. Wieland G. Anner A. Wettstein G. Cainelli D. Arigoni O. Jeger 《Cellular and molecular life sciences : CMLS》1960,16(1):21-24
Summary The preparation of the (18 11)-lactone of
5-3-ethylenedioxy-11-hydroxy-21-acetoxy-20-oxo-pregnen-18-oic acid (XV) is reported. Since this compound has previously been transformed into aldosterone, the reactions described represent the first partial synthesis of this important hormone from readily available 18-unsubstituted natural steroids.
Über Steroide, 163. Mitteilung; 162. Mitteilung vgl.P. Wieland, K. Heusler undA. Wettstein, Helv. chim. Acta43 (1960), im Druck; XV. Mitteilung überSynthesen in der Aldosteron-Reihe; XIV. Mitteilung vgl.J. Schmidlin undA. Wettstein, Helv. chim. Acta42, 2636 (1959).
Steroide und Sexualhormone, 215, Mitteilung; 214. Mitteilung vgl.B. Kamber, G. Cainelli, D. Arigoni undO. Jeger, Helv. chim. Acta43 (1960), im Druck. 相似文献
Über Steroide, 163. Mitteilung; 162. Mitteilung vgl.P. Wieland, K. Heusler undA. Wettstein, Helv. chim. Acta43 (1960), im Druck; XV. Mitteilung überSynthesen in der Aldosteron-Reihe; XIV. Mitteilung vgl.J. Schmidlin undA. Wettstein, Helv. chim. Acta42, 2636 (1959).
Steroide und Sexualhormone, 215, Mitteilung; 214. Mitteilung vgl.B. Kamber, G. Cainelli, D. Arigoni undO. Jeger, Helv. chim. Acta43 (1960), im Druck. 相似文献
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J. Kalvoda J. Schmidlin G. Anner A. Wettstein 《Cellular and molecular life sciences : CMLS》1962,18(9):398-400
Summary 18-Hydroxyprogesterone (VII) and the corresponding 18-aldehyde (IX), hitherto only accessible with difficulty from natural 18-substituted steroids, have been synthesized starting from progesterone.
Über Steroide, 188. Mitt.
187. Mitt. s.Ch. Meystre, K. Heusler, J. Kalvoda, P. Wieland, G. Anner undA. Wettstein, Helv. chim. Acta45, 1317 (1962). 相似文献
Über Steroide, 188. Mitt.
187. Mitt. s.Ch. Meystre, K. Heusler, J. Kalvoda, P. Wieland, G. Anner undA. Wettstein, Helv. chim. Acta45, 1317 (1962). 相似文献
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