Collect. Czech. Chem. Commun. 1996, 61, 1386-1395
https://doi.org/10.1135/cccc19961386

trans-Hydrindanes by Reduction: Synthesis of Dihydro-B-nortestosterone

Alexander Kasala, Hana Chodounskáa and Wojciech J. Szczepekb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10 Prague 6, Czech Republic
b Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, Poland

Individual author index pages


Other CCCC articles of these authors

  • Eva Šťastná, Hana Chodounská*, Vladimír Pouzar, Jiřina Borovská and Ladislav Vyklický, Jr.
    Synthesis of pregnane 3-carboxylic acids via Pd-catalyzed alkoxycarbonylation and their effect on NMDA receptor activity
    2011, Vol. 76, Issue 9, pp. 1141–1161 [Abstract]
  • Vojtěch Kapras, Eva Šťastná, Hana Chodounská*, Vladimír Pouzar and Zdena Krištofíková
    Preparation of steroid sulfamates and their interaction with GABAA receptor
    2009, Vol. 74, Issue 4, pp. 643–650 [Abstract]
  • Pavel Herrmann, Jaroslav Kvíčala, Vladimír Pouzar and Hana Chodounská*
    Synthesis of Fluorinated Steroids Using a Novel Fluorinating Reagent Tetrabutylammonium Difluorodimethylphenylsilicate (TAMPS)
    2008, Vol. 73, Issue 12, pp. 1825–1834 [Abstract]
  • Miloš Buděšínský, Jan Fajkoš, Jaroslav Günter and Alexander Kasal*
    Synthesis, Reactions, Conformation Analysis, and NMR Spectra of 5,10-Epoxy-5ξ,10ξ-estrane-3,17-diones
    2005, Vol. 70, Issue 4, pp. 507–518 [Abstract]
  • Libor Matyáš, Alexander Kasal*, Zoila Babot Riera and Cristina E. Sunol
    Effects of 3α-Amino-5α-pregnan-20-one on GABAA Receptor: Synthesis, Activity and Cytotoxicity
    2004, Vol. 69, Issue 7, pp. 1506–1516 [Abstract]
  • Barbora Slavíková*, Alexander Kasal, Hana Chodounská and Zdena Krištofíková
    3α-Fluoro Analogues of "Allopregnanolone" and Their Binding to GABAA Receptors
    2002, Vol. 67, Issue 1, pp. 30–46 [Abstract]
  • Hana Chodounská, Miloš Buděšínský, Romana Šídová, Miroslav Šíša, Alexander Kasal and Ladislav Kohout*
    Simple NMR Determination of 5α/5β Configuration of 3-Oxosteroids
    2001, Vol. 66, Issue 10, pp. 1529–1544 [Abstract]
  • Ladislav Kohout*, Hana Chodounská, Tomáš Macek and Miroslav Strnad
    Synthesis of (20S)-2α,3α-Dihydroxy-6-oxo-7-oxa-7a-homo-5α-pregnane-20-carboxylic Acid as a Brassinosteroid Part of Ligands for Binding to Affinity Chromatography Carriers
    2000, Vol. 65, Issue 11, pp. 1754–1761 [Abstract]
  • Hana Chodounská* and Alexander Kasal
    Allopregnanolone Derivatives: Synthesis of 3α-Hydroxy-7a-homo-5α-pregnan-20-one
    2000, Vol. 65, Issue 7, pp. 1156–1162 [Abstract]
  • Alexander Kasal*, Miloš Buděšínský, Jan Pelnař, Michael A. Bruck* and Michael F. Brown
    Structures and Synthesis of 4a-Homo-7,19-dinorsteroids, X-Ray Crystallography and NMR Spectroscopy
    1999, Vol. 64, Issue 12, pp. 2019–2034 [Abstract]
  • Barbora Slavíková* and Alexander Kasal
    Epalons: Synthesis of New 16α-Carboxymethyl Derivatives
    1999, Vol. 64, Issue 9, pp. 1479–1484 [Abstract]
  • Alexander Kasal
    Epalons: Synthesis of 7-Norallopregnanolone
    1999, Vol. 64, Issue 9, pp. 1471–1478 [Abstract]
  • Barbora Slavíková, Alexander Kasal* and Miloš Buděšínský
    Autoxidation vs Hydrolysis in 16α-Acyloxy Steroids
    1999, Vol. 64, Issue 7, pp. 1125–1134 [Abstract]
  • Jacek W. Morzycki, Agnieszka Gryszkiewicz, Zenon Lotowski and Wojciech J. Szczepek
    Reduction of 2-Nitro-5α-cholestan-3-one, Its Enol Tautomer and 2-Nitro-5α-cholest-2-en-3-amine Derivatives. Synthesis of Bis-Steroidal Pyrazines
    1998, Vol. 63, Issue 10, pp. 1589–1596 [Abstract]
  • Alexander Kasal, Jiří Polman and Miloš Buděšínský
    Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes
    1998, Vol. 63, Issue 10, pp. 1549–1563 [Abstract]
  • Hana Chodounská and Alexander Kasal
    Epalons: Synthesis of 3α,7α-Dihydroxy-5α-pregnan-20-one
    1998, Vol. 63, Issue 10, pp. 1543–1548 [Abstract]
  • Romana Šídová, Karel Stránský, Alexander Kasal, Barbora Slavíková and Ladislav Kohout
    Long-Range Effect of 17-Substituents in 3-Oxo Steroids on 4,5-Double Bond Hydrogenation
    1998, Vol. 63, Issue 10, pp. 1528–1542 [Abstract]
  • Barbora Slavíková, Alexander Kasal and Ladislav Kohout
    N-Benzoyl-N-methylandrostan-17β-amines; 20-Aza Analogues of Brassinolide
    1998, Vol. 63, Issue 5, pp. 655–661 [Abstract]
  • Alexander Kasal, Barbora Slavíková, Ladislav Kohout and Miloš Buděšínský
    The Synthesis of A-Homo-B-norandrostanes: The Effect of a Hydroxyl on the Course of Hydrogenation of the ∆9-Double Bond
    1997, Vol. 62, Issue 10, pp. 1631–1641 [Abstract]
  • Barbora Slavíková, Alexander Kasal and Miloš Buděšínský
    Dihydrotestosterone with an Ammonium Centre in the Position 16β
    1997, Vol. 62, Issue 4, pp. 656–664 [Abstract]
  • Hana Chodounská, Alexander Kasal, David Šaman and Karel Ubik
    One-Pot Deuteration and Reduction of Ketones in the Synthesis of [16,16,17-2H3]-Epitestosterone
    1996, Vol. 61, Issue 7, pp. 1037–1046 [Abstract]
  • Ladislav Kohout, Alexander Kasal and Miroslav Strnad
    Pregnane-Type Brassinosteroids with a Four-Carbon Ester Functionality in Position 20
    1996, Vol. 61, Issue 6, pp. 930–940 [Abstract]
  • Oldřich Lapčík, Richard Hampl, Martin Hill, Luboslav Stárka, Alexander Kasal, Vladimír Pouzar and Zdeněk Putz
    Radioimmunological and Chromatographic Properties of Tyrosine Methyl Ester Conjugates with Stereoisomeric Steroid Carboxy Derivatives
    1996, Vol. 61, Issue 5, pp. 799–807 [Abstract]
  • Alexander Kasal and Miloš Buděšínský
    Partial Modifications of Hydroxy Groups in 5-Methyl-5β-estr-9-ene Derivatives
    1996, Vol. 61, Issue 2, pp. 276–287 [Abstract]
  • Alexander Kasal, Ladislav Kohout and Michal Lebl
    Synthesis of a Scaffold for the Creation of Non-Peptide Libraries
    1995, Vol. 60, Issue 12, pp. 2147–2155 [Abstract]
  • Ladislav Kohout and Alexander Kasal
    7a-Keto-B-homotestosterone and 7a-Keto-B-homoepitestosterone
    1994, Vol. 59, Issue 3, pp. 649–657 [Abstract]
  • Hana Chodounská, Barbora Slavíková and Alexander Kasal
    Synthesis of Some Epitestosterone Analogues
    1994, Vol. 59, Issue 2, pp. 435–443 [Abstract]
  • Hana Chodounská and Vladimír Pouzar
    Preparation of 3-(6-Deoxy-β-D-glucopyranosyloxy) and 3-(6-Deoxy-α-L-mannopyranosyloxy)androstane Derivatives with Unsaturated Side Chain in Position 17β
    1993, Vol. 58, Issue 12, pp. 3000–3008 [Abstract]
  • Alexander Kasal
    Synthesis of 17α-Hydroxy Steroids: B-Norepitestosterone
    1993, Vol. 58, Issue 9, pp. 2202–2210 [Abstract]
  • Alexander Kasal and Světlana Pásztorová
    Synthesis of RIA Haptens: 3α,11α-Dihydroxy-5α-pregnan-20-one 11-Hemisuccinate
    1993, Vol. 58, Issue 3, pp. 619–628 [Abstract]
  • Alexander Kasal, Květa Fuksová and Vladimír Pouzar
    Preparation of Unlabelled and [3H]-Labelled Epitestosterone and Its Metabolites
    1993, Vol. 58, Issue 3, pp. 600–611 [Abstract]
  • Alexander Kasal, Richard Hampl, Zdeněk Putz, Ladislav Kohout and Luboslav Stárka
    Preparation and Properties of Three Immunogens with a Spacer on the β-Side of the Steroid Skeleton and the Effect of Immunogen Structure on Specificity of the Obtained Antisera
    1992, Vol. 57, Issue 10, pp. 2166–2173 [Abstract]
  • Vladimír Pouzar, Hana Chodounská, Ivan Černý and Pavel Drašar
    Derivatives of 5α-androstan-3α- and 3β-ol with acrylonitrile side chain
    1991, Vol. 56, Issue 12, pp. 2906–2916 [Abstract]
  • Jiří Polman and Alexander Kasal
    The synthesis of 5-methyl-19-nor-5β-pregna-9,16-diene-3,20-dione, 5-methyl-19-nor-5β-pregna-9,10-diene-3,6,20-trione and their analogues with annellated E ring
    1991, Vol. 56, Issue 12, pp. 2892–2905 [Abstract]
  • Miloš Buděšínský, Alexander Kasal, Želimír Procházka, Huynh Kim Thoa, Soňa Vašíčková and Pavel Kočovský
    Revision of the structure of 3-methoxy-14α-hydroxy-D-homo-1,3,5-(10)-estratrien-17a-one. A simple 1H NMR method for the determination of configuration of hydroxy group in position 5 and/or 14 of the D-homo-steroid skeleton
    1991, Vol. 56, Issue 7, pp. 1512–1524 [Abstract]
  • Alexander Kasal, Jenny Pokorná and Jaroslav Zajíček
    3β,11α,17-Trihydroxy-5-pregnen-20-one 11-hemisuccinate as a haptene for RIA of "17α-hydroxypregnenolone"
    1991, Vol. 56, Issue 6, pp. 1340–1347 [Abstract]
  • Alexander Kasal, Jaroslav Podlaha and Jaroslav Zajíček
    A-homo-B,19-dinorandrostanes from 6β-methanesulfonyloxy-5-methyl-19-nor-5β-androst-9-ene derivatives
    1991, Vol. 56, Issue 5, pp. 1070–1086 [Abstract]
  • Jiří Polman and Alexander Kasal
    Synthesis of 5-methyl-19-nor-5β-pregn-9-ene derivatives
    1990, Vol. 55, Issue 7, pp. 1783–1791 [Abstract]
  • Hana Chodounská and Vladimír Pouzar
    Preparation of 3-(β-D-galactopyranosyloxy)androstane derivatives with unsaturated side chain in position 17β
    1990, Vol. 55, Issue 6, pp. 1639–1646 [Abstract]
  • Vladimír Pouzar, Hana Chodounská, Dalibor Sameš, Pavel Drašar and Miroslav Havel
    Derivatives of 5α-androstan-3α- and 3β-ol with acrylate side chain
    1990, Vol. 55, Issue 5, pp. 1243–1256 [Abstract]
  • Alexander Kasal
    Antiandrogenic A-homo-B,19-dinorandrostanes from 5β-methyl-19-norandrost-9-enes with different substituents in positions 3 and 17
    1989, Vol. 54, Issue 8, pp. 2218–2228 [Abstract]
  • Alexander Kasal and Jaroslav Zajíček
    Spontaneous transannular reaction in Δ9-unsaturated A-homo-B,19-dinorsteroids
    1989, Vol. 54, Issue 5, pp. 1327–1335 [Abstract]
  • Alexander Kasal
    Antiandrogenic A-homo-B,19-dinor-analogues of androgens from 6β-chloro-5-methyl-19-nor-5β-androst-9-enes
    1989, Vol. 54, Issue 5, pp. 1318–1326 [Abstract]
  • Eva Klinotová, Helena Pavlíková, Martina Pressová, Hana Chodounská, Jiří Klinot, Jiří Protiva and Alois Vystrčil
    E-seco-Acids of pentacyclic triterpenoids. Oxidative cleavage of ring E in 3β-acetoxy-21-oxo-18α,19βH-ursan-28→20β-olide
    1987, Vol. 52, Issue 11, pp. 2744–2752 [Abstract]
  • Alexander Kasal and Jaroslav Zajíček
    Solvolysis of Westphalen-type compounds
    1986, Vol. 51, Issue 7, pp. 1462–1475 [Abstract]
  • Ladislav Kohout, Vijay Kumar Sethi, Jaroslav Zajíček and Alexander Kasal
    Solvolytic reactions of empiric 3-methanesulfonyloxy-7-benzoyloxy-5β,6β-cyclopropanocholestanes
    1986, Vol. 51, Issue 2, pp. 436–446 [Abstract]
  • Alexander Kasal, Ladislav Kohout and Jiří Filip
    4,5-Secoandrostanes by Eschenmoser's reaction
    1985, Vol. 50, Issue 6, pp. 1402–1414 [Abstract]
  • Luboslav Stárka, Alexander Kasal, Marie Bičíková and Richard Hampl
    Preparation and synandrogenic activity of 17β-hydroxy-4,5-seco-5-androsten-3-one
    1984, Vol. 49, Issue 12, pp. 2942–2947 [Abstract]
  • Alexander Kasal and Jorga Smolíková
    Photochemical 6β-hydroxylation of 11β-hydroxy-4-androstene-3,17-dione
    1984, Vol. 49, Issue 12, pp. 2932–2941 [Abstract]
  • Alexander Kasal
    A new type of A-homo-B-norcholestane derivatives
    1984, Vol. 49, Issue 4, pp. 892–902 [Abstract]
  • Ladislav Kohout and Alexander Kasal
    Electrophilic addition to the 5,6-double bond in A-nor-3,5-secosteroids
    1983, Vol. 48, Issue 7, pp. 2051–2063 [Abstract]
  • Alexander Kasal, Luboš Stárka, Richard Hampl and Ladislav Kohout
    Preparation and pharmacological properties of 4,5-secopregnane-3,20-dione and its derivatives
    1983, Vol. 48, Issue 7, pp. 2040–2050 [Abstract]
  • Alexander Kasal
    4-Thia-5-cholesten-3-one and some further steroidal δ-thioenol lactones
    1983, Vol. 48, Issue 5, pp. 1489–1498 [Abstract]
  • Ladislav Kohout, Alexander Kasal, Vlastimil Šanda and Helena Velgová
    Rearrangement of the 16,17-cyclopropano derivatives
    1983, Vol. 48, Issue 1, pp. 173–183 [Abstract]
  • Alexander Kasal
    Desulfuration of steroidal thians
    1982, Vol. 47, Issue 11, pp. 3148–3159 [Abstract]
  • Antonín Trka and Alexander Kasal
    Inductive effect in EI-mass spectra of some 5,6-dihalogenides and 5,6-halohydrins of 5α-cholestan-3β-ol and 3β-acetoxy-5α-cholestane
    1982, Vol. 47, Issue 11, pp. 2946–2960 [Abstract]
  • Alexander Kasal and Ladislav Kohout
    4,5-Secoanalogues of dihydrotestosterone with a cyclopropane ring in the position 5(6)
    1982, Vol. 47, Issue 1, pp. 130–143 [Abstract]
  • Alexander Kasal
    Hydrogenation of 12-oxo-5β-chol-9(11)-enates on platinum
    1981, Vol. 46, Issue 8, pp. 1839–1849 [Abstract]
  • Alexander Kasal and Antonín Trka
    Splitting off of water from the molecular ions of steroidal cyclopropyl ketones
    1980, Vol. 45, Issue 11, pp. 2985–2997 [Abstract]
  • Alexander Kasal
    Analogues of androgens with the open ring A
    1980, Vol. 45, Issue 9, pp. 2541–2549 [Abstract]
  • Antonín Trka and Alexander Kasal
    Electron impact mass spectra of some vicinal trans-dihalo- and trans-hydroxyhalocholestanes
    1980, Vol. 45, Issue 6, pp. 1720–1733 [Abstract]
  • Alexander Kasal
    Deoxygenation at the carbon C(5) of 3,6-cyclo-A-nor-3,5-secoandrostanes
    1979, Vol. 44, Issue 5, pp. 1619–1629 [Abstract]
  • Alexander Kasal
    Synthesis of 3,6-cyclo-A-nor-3,5-secoandrostanes
    1978, Vol. 43, Issue 7, pp. 1778–1792 [Abstract]
  • Alexander Kasal
    Reduction of some 3,6-cyclo-A-nor-3,5-seco-6β-cholestanes
    1978, Vol. 43, Issue 2, pp. 498–510 [Abstract]