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INVESTIGATIONS ON STEROIDS. VIII. LOWER HOMOLOGS OF HORMONES OF THE PREGNANE SERIES: 10-NOR-11-DESOXY-CORTICOSTERONE ACETATE AND 10-NORPROGESTERONE1

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    INVESTIGATIONS ON STEROIDS. VIII. LOWER HOMOLOGS OF HORMONES OF THE PREGNANE SERIES: 10-NOR-11-DESOXY-CORTICOSTERONE ACETATE AND 10-NORPROGESTERONE1
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    Cite this: J. Org. Chem. 1944, 09, 5, 435–456
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    https://doi.org/10.1021/jo01187a009
    Published September 1, 1944
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    This article is cited by 37 publications.

    1. Kim Søholm Halskov, Bjarke S. Donslund, Sebastian Barfüsser, Karl Anker Jørgensen. Organocatalytic Asymmetric Formation of Steroids. Angewandte Chemie 2014, 126 (16) , 4221-4225. https://doi.org/10.1002/ange.201400203
    2. Kim Søholm Halskov, Bjarke S. Donslund, Sebastian Barfüsser, Karl Anker Jørgensen. Organocatalytic Asymmetric Formation of Steroids. Angewandte Chemie International Edition 2014, 53 (16) , 4137-4141. https://doi.org/10.1002/anie.201400203
    3. Carl Djerassi. The Oppenauer Oxidation. 2011, 207-272. https://doi.org/10.1002/0471264180.or006.05
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    8. Carl Djerassi. Steroid research at Syntex: “the Pill” and cortisone. Steroids 1992, 57 (12) , 631-641. https://doi.org/10.1016/0039-128X(92)90016-3
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    21. Carl Djerassi. Steroid Oral Contraceptives. Science 1966, 151 (3714) , 1055-1061. https://doi.org/10.1126/science.151.3714.1055
    22. IRA RINGLER. Activities of Adrenocorticosteroids in Experimental Animals and Man. 1964, 227-349. https://doi.org/10.1016/B978-1-4832-3034-4.50012-0
    23. Albert Von Wartburg. Über die Autoxydation des Strophanthidins (3. Teil) Abbau von 10 β‐Hydroxy‐19‐norperiplogenin zu Östron. 51. Mitteilung über Herglzkoside. Helvetica Chimica Acta 1963, 46 (2) , 591-601. https://doi.org/10.1002/hlca.19630460219
    24. N R Stephenson. The Importance of the 19-Methyl and the C(20) Ketone Groups for the Thymolytic Activity of the Adrenocortical Steroids. Journal of Pharmacy and Pharmacology 1960, 12 (1) , 416-418. https://doi.org/10.1111/j.2042-7158.1960.tb12683.x
    25. R. Anliker, M. Müller, M. Perelman, J. Wohlfahrt, H. Heusser. Über Steroide und Sexualhormone. 210. Mitteilung. Die Synthese von 18‐Nor‐progesteron und des 13α, 17α‐18‐Nor‐progresterons. Helvetica Chimica Acta 1959, 42 (3) , 1071-1085. https://doi.org/10.1002/hlca.19590420343
    26. Daniel A. McGinty, Carl Djerassi. SOME CHEMICAL AND BIOLOGICAL PROPERTIES OF 19-NOR-17?-ETHYNYLTESTOSTERONE. Annals of the New York Academy of Sciences 1958, 71 (5 New Steriod C) , 500-515. https://doi.org/10.1111/j.1749-6632.1958.tb46781.x
    27. G. Winston Barber, Maximilian Ehrenstein. Untersuchungen über Steroide XXVIII. Synthese von 19‐nor‐10ξ.14β.17α‐Progesteron und 19‐nor‐11‐Desoxy‐10ξ.14β.17α‐Corticosteron aus Strophanthidin. Justus Liebigs Annalen der Chemie 1957, 603 (1) , 89-109. https://doi.org/10.1002/jlac.19576030111
    28. A. Wettstein, G. Anner. Advances in the field of adrenal cortical hormones. Experientia 1954, 10 (10) , 397-416. https://doi.org/10.1007/BF02318502
    29. Hs. H. Günthard, E. Beriger, Ch. R. Engel, H. Heusser. Über Steroide und Sexualhormone. 188. Mitteilung. Eine neue Variante der Synthese des biologisch hoch aktiven Gestagens 17α‐Methyl‐progesteron. Helvetica Chimica Acta 1952, 35 (7) , 2437-2444. https://doi.org/10.1002/hlca.19520350732
    30. A. Heusner. Die Stereochemie der natürlichen Steroide. Angewandte Chemie 1951, 63 (3) , 59-70. https://doi.org/10.1002/ange.19510630303
    31. H. Heusser, K. Eichenberger, A. B. Kulkarni. Über Steroide und Sexualhormone. 165. Mitteilung. Über die Synthese von 14‐Allo‐17‐epi‐testosteron. Helvetica Chimica Acta 1949, 32 (6) , 2145-2151. https://doi.org/10.1002/hlca.19490320640
    32. A. Buzas, T. Reichstein. Die zwei durch Abbau von Strophanthidin erhältlichen, an C‐17 raumisomeren 3 β, 5, 14‐Trioxy‐14‐ iso ‐21‐norpregnan‐19, 20‐disäuren. Glyoside und Aglykone, 29. Mitteilung. Helvetica Chimica Acta 1948, 31 (1) , 84-90. https://doi.org/10.1002/hlca.19480310117
    33. Pl. A. Plattner, H. Heusser, A. Segre. Über Steroide und Sexualhormone. 148. Mitteilung. Synthese des 14‐Allo‐17‐iso‐progesterons. Helvetica Chimica Acta 1948, 31 (1) , 249-256. https://doi.org/10.1002/hlca.19480310146
    34. P. Speiser, T. Reichstein. Konfiguration des Periplogenins und Alloperiplogenins II. Glykoside und Aglykone. Helvetica Chimica Acta 1948, 31 (2) , 622-629. https://doi.org/10.1002/hlca.19480310243
    35. Ch. Meystre, E. Tschopp, A. Wettstein. Über Steroide. 81. Mitteilung. Über 11‐Dehydro‐Progesteron, das wirksamste Gestagen. Helvetica Chimica Acta 1948, 31 (6) , 1463-1469. https://doi.org/10.1002/hlca.19480310604
    36. K. MIESCHER. On the Relation of Activity to Constitution in the Sexogens, with Special Reference to the Doisynolic Acids. 1948, 47-69. https://doi.org/10.1016/B978-1-4831-9891-0.50005-1
    37. Willard M. Allen, Maximilian Ehrenstein. 10-Nor-Progesterone, a Physiologically Active Lower Homolog of Progesterone. Science 1944, 100 (2594) , 251-252. https://doi.org/10.1126/science.100.2594.251
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    Cite this: J. Org. Chem. 1944, 09, 5, 435–456
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo01187a009
    Published September 1, 1944
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