Reaction of lead tetraacetate with steroidal α,α′-dihydroxy ketones in alcoholic media
作者： E. Caspi , W. Schmid , T.A. Wittstruck
DOI: 10.1016/0040-4020(61)80078-1
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摘要: Abstract The main production of the reaction steroids with a dihydroxy acetone moiety and lead tetraacetate in presence methanol or ethanol was corresponding etio-ester. 17-ketosteroids were obtained as minor products. With higher alcohols addition to etio-esters 17α-formoxy-etio-esters isolated. Partial acetylation C21 hydroxyl group also observed. tertiary-butyl alcohol, C-21 cleavage occurred.
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Rudolf Criegee, Ludwig Kraft, Bodo Rank, Die Glykolspaltung, ihr Mechanismus und ihre Anwendung auf chemische Probleme Justus Liebig's Annalen der Chemie. ,vol. 507, pp. 159- 197 ,(1933) , 10.1002/JLAC.19335070115
J. S. G. Cox, E. O. Bishop, R. E. Richards, 988. Proton resonance spectra of some 11-keto-steroids Journal of The Chemical Society (resumed). pp. 5118- 5127 ,(1960) , 10.1039/JR9600005118
Rudolf Criegee, Oxydation ungesättigter Kohlenwasserstoffe mit Blei (4)‐salzen European Journal of Organic Chemistry. ,vol. 481, pp. 263- 302 ,(1930) , 10.1002/JLAC.19304810117
G. Cainelli, M. Lj. Mihailović, D. Arigoni, O. Jeger, Über Steroide und Sexualhormone. 211. Mitteilung. Direkte Einführung einer Sauerstoffunktion in die Methylgruppe C‐18 im intakten Steroidgerüst Helvetica Chimica Acta. ,vol. 42, pp. 1124- 1127 ,(1959) , 10.1002/HLCA.19590420346
Eliahu Caspi, Frank Ungar, Ralph Dorfman, Notes - Degradation of 3α,17α,21-Trihydroxypregnan-20-oneC14 Biosynthesized from Acetate-1-C14 by a Cushing's Patient Journal of Organic Chemistry. ,vol. 22, pp. 326- 327 ,(1957) , 10.1021/JO01354A604
W. Rigby, 389. Oxidations with sodium bismuthate : glycol fission and related reactions Journal of the Chemical Society (Resumed). pp. 1907- 1913 ,(1950) , 10.1039/JR9500001907
William A. Mosher, Clifton L. Kehr, The Oxidation of Aliphatic Esters with Lead Tetraacetate1 Journal of the American Chemical Society. ,vol. 82, pp. 5342- 5345 ,(1960) , 10.1021/JA01505A018
E. J. Corey, R. W. Wiiite, CATIONIC DISPLACEMENT OF HYDROGEN BY OXYGEN AT A SATURATED CARBON ATOM Journal of the American Chemical Society. ,vol. 80, pp. 6686- 6686 ,(1958) , 10.1021/JA01557A056
Rudolf Criegee, Eberhard Büchner, Die Geschwindigkeit der Glykolspaltung mit BleiIV‐acetat in Abhängigkeit vom Lösungsmittel European Journal of Inorganic Chemistry. ,vol. 73, pp. 563- 571 ,(1940) , 10.1002/CBER.19400730602
K. Heusler, J. Kalvoda, Ch. Meystre, P. Wieland, G. Anner, A. Wettstein, G. Cainelli, D. Arigoni, O. Jeger, Partialsynthese von Aldosteron. Über Steroide, 177. Mitteilung Helvetica Chimica Acta. ,vol. 44, pp. 502- 517 ,(1961) , 10.1002/HLCA.19610440221