Collect. Czech. Chem. Commun. 1987, 52, 1026-1042
https://doi.org/10.1135/cccc19871026

Alternative syntheses of 2α,3α,17β-trihydroxy-7-oxa-B-homo-5α-androstan-6-one and some androstane brassinolide analogs

Ladislav Kohouta, Václav Černýa and Miroslav Strnadb

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Institute of Experimental Botany, Czechoslovak Academy of Sciences, 772 00 Olomouc

Individual author index pages


Other CCCC articles of these authors

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    2002, Vol. 67, Issue 2, pp. 257–266 [Abstract]
  • Hana Chodounská, Miloš Buděšínský, Romana Šídová, Miroslav Šíša, Alexander Kasal and Ladislav Kohout*
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    2001, Vol. 66, Issue 10, pp. 1529–1544 [Abstract]
  • Ladislav Kohout*, Hana Chodounská, Tomáš Macek and Miroslav Strnad
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    2000, Vol. 65, Issue 11, pp. 1754–1761 [Abstract]
  • Jaroslava Hniličková* and Ladislav Kohout
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    2000, Vol. 65, Issue 3, pp. 380–384 [Abstract]
  • Carme Brosa, Ismael Zamora, Emma Terricabras and Ladislav Kohout
    The Effect of Electrostatic Properties and Abibility to Form Hydrogen-Bonds on the Activity of Brassinosteroid Side-Chain Analogs
    1998, Vol. 63, Issue 10, pp. 1635–1645 [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
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    1998, Vol. 63, Issue 5, pp. 655–661 [Abstract]
  • Ladislav Kohout, Barbora Slavíková and Miroslav Strnad
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    1998, Vol. 63, Issue 5, pp. 646–654 [Abstract]
  • Lucie Dalibová and Ladislav Kohout
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    1998, Vol. 63, Issue 4, pp. 549–556 [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]
  • 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]
  • 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
    7-Oxo-7a-oxa-brassinosteroids with Cholestane Side-Chain
    1994, Vol. 59, Issue 5, pp. 1219–1225 [Abstract]
  • Ladislav Kohout and Alexander Kasal
    7a-Keto-B-homotestosterone and 7a-Keto-B-homoepitestosterone
    1994, Vol. 59, Issue 3, pp. 649–657 [Abstract]
  • Ladislav Kohout
    New Method of Preparation of Brassinosteroids
    1994, Vol. 59, Issue 2, pp. 457–460 [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]
  • Ladislav Kohout and Miroslav Strnad
    Brassinosteroids with Ester Function with Five Carbon Atoms at the 20 Position
    1992, Vol. 57, Issue 8, pp. 1731–1738 [Abstract]
  • Václav Černý and Miloš Buděšínský
    A route to 24-epibrassinolide from ergosterol avoiding the use of osmium tetroxide
    1990, Vol. 55, Issue 11, pp. 2738–2755 [Abstract]
  • Ladislav Kohout
    Syntheis of brassino steroids with a five carbon atom ester functionality in position 17
    1989, Vol. 54, Issue 12, pp. 3348–3359 [Abstract]
  • Václav Černý
    An alternative route to 2α,3α-diols from 2,3-unsaturated 5α-steroids avoiding the use of osmium tetroxide
    1989, Vol. 54, Issue 8, pp. 2211–2217 [Abstract]
  • Ladislav Kohout
    7-Methanesulfonyloxy-3α,5-cyclo-5α-cholestanes
    1989, Vol. 54, Issue 4, pp. 1028–1035 [Abstract]
  • Ladislav Kohout and Miroslav Strnad
    Brassinolide analogues without side chain
    1989, Vol. 54, Issue 4, pp. 1019–1027 [Abstract]
  • Václav Černý, Miloš Buděšínský, Miloš Ryba and František Tureček
    A contribution to peroxy acid oxidation of α,β-unsaturated ketones and linearly conjugated dienones: Reactions in the cholestane series
    1988, Vol. 53, Issue 7, pp. 1549–1567 [Abstract]
  • Ladislav Kohout, Helena Velgová, Miroslav Strnad and Miroslav Kamínek
    Brassino steroids with androstane and pregnane skeleton
    1987, Vol. 52, Issue 2, pp. 476–486 [Abstract]
  • Václav Černý, Jaroslav Zajíček and Miroslav Strnad
    2α,3α-Dihydroxy-7-oxa-6-oxo-B-homo-5α-pregnan-21-oic acid and its derivatives as brassinolide analogues
    1987, Vol. 52, Issue 1, pp. 215–222 [Abstract]
  • Ladislav Kohout
    Solvolytic reactions of epimeric 3-methanesulfonyloxy-7-benzoyloxy-5α,6α-cyclopropanocholestanes
    1986, Vol. 51, Issue 10, pp. 2222–2231 [Abstract]
  • Václav Černý, Miroslav Strnad and Miroslav Kamínek
    Preparation of 2α,3α-dihydroxy-7-oxa-6-oxo-23,24-dinor-B-homo-5α-cholanic acid, its esters and amides as brassinolide analogues
    1986, Vol. 51, Issue 3, pp. 687–697 [Abstract]
  • Ladislav Kohout and Miroslav Strnad
    Brassinosteroids with a cholestane side chain
    1986, Vol. 51, Issue 2, pp. 447–458 [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]
  • Ladislav Kohout
    The synthesis of 5,6-cyclopropanocholestanes with oxygen functions in positions 3 and 7
    1986, Vol. 51, Issue 2, pp. 429–435 [Abstract]
  • Alexander Kasal, Ladislav Kohout and Jiří Filip
    4,5-Secoandrostanes by Eschenmoser's reaction
    1985, Vol. 50, Issue 6, pp. 1402–1414 [Abstract]
  • Helena Velgová and Ladislav Kohout
    6,7-Secoandrostane derivatives
    1985, Vol. 50, Issue 4, pp. 962–972 [Abstract]
  • Ladislav Kohout and Jaroslav Zajíček
    Lead tetraacetate oxidation of 3β-acetoxy-B-homo-5α-cholestan-7aβ-ol
    1984, Vol. 49, Issue 1, pp. 301–305 [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]
  • 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]
  • Václav Černý and Pavel Kočovský
    Neighboring group participation in hypobromous acid addition to 19-substituted 5α-cholest-1-enes and in acid cleavage of their epoxy analogs
    1982, Vol. 47, Issue 11, pp. 3062–3076 [Abstract]
  • Miloslav Frumar, Gustáv Plesch, Eva Černošková, Václav Černý, Ladislav Tichý and Helena Tichá
    EPR spectra and defect states in glasses of the GexS100-x system
    1982, Vol. 47, Issue 7, pp. 1787–1793 [Abstract]
  • Ladislav Kohout, Vlastimil Šanda and Jan Fajkoš
    Synthesis of two isomeric 16,17-cyclopropano derivatives of 5-pregnene
    1982, Vol. 47, Issue 5, pp. 1503–1513 [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]
  • Pavel Kočovský, František Tureček and Václav Černý
    Mechanism of acid cleavage of some steroid epoxides. Competition between neighboring group participation and external nucleophile attack
    1982, Vol. 47, Issue 1, pp. 124–129 [Abstract]
  • Pavel Kočovský, František Tureček and Václav Černý
    Mechanism of hypobromous acid addition to unsaturated steroids. Competition between neighboring group participation and external nucleophile attack
    1982, Vol. 47, Issue 1, pp. 117–123 [Abstract]
  • Ladislav Kohout
    Synthesis of 5,6-cyclopropanocholestane derivatives with an oxygen function in position 7
    1981, Vol. 46, Issue 8, pp. 1828–1838 [Abstract]
  • Pavel Kočovský and Václav Černý
    A modified route to intermediates in partial syntheses of digitoxigenin and xysmalogenin
    1981, Vol. 46, Issue 2, pp. 446–451 [Abstract]
  • Pavel Kočovský and Václav Černý
    Participation of 19-substituents in acid cleavage of steroidal 3α,4α- and 4α,5α-epoxides
    1980, Vol. 45, Issue 11, pp. 3199–3209 [Abstract]
  • Pavel Kočovský and Václav Černý
    Participation of 19-substituents in acid cleavage of steroidal 5α,6α-epoxides
    1980, Vol. 45, Issue 11, pp. 3190–3198 [Abstract]
  • Pavel Kočovský and Václav Černý
    Participation of 19-substituents in hypobromous acid addition to 3,4- and 4,5-unsaturated steroids
    1980, Vol. 45, Issue 11, pp. 3030–3038 [Abstract]
  • Pavel Kočovský and Václav Černý
    Participation of 19-substituents in electrophilic additions. influence of 3β-substitution on hypobromous acid addition to 5,6-unsaturated steroids
    1980, Vol. 45, Issue 11, pp. 3023–3029 [Abstract]
  • František Tureček and Ladislav Kohout
    The stereospecific loss of water from B-homocholestanols under electron impact
    1980, Vol. 45, Issue 9, pp. 2433–2442 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Analogues of androgens with a cyclopropane ring in 6α,7α-position
    1980, Vol. 45, Issue 7, pp. 1974–1981 [Abstract]
  • Pavel Kočovský and Václav Černý
    Synthesis of 14-deoxy-14α-strophanthidol
    1980, Vol. 45, Issue 3, pp. 921–926 [Abstract]
  • Pavel Kočovský, Ladislav Kohout and Václav Černý
    Participation of 19-substituents in electrophilic additions to 6,7-unsaturated 5α-cholestane and B-homo 5α-cholestane derivatives; A case of competition between the participation of an ambident neighboring group and external nucleophile attack
    1980, Vol. 45, Issue 2, pp. 559–583 [Abstract]
  • Vlastimil Šanda, Ladislav Kohout and Jan Fajkoš
    5,7-Cyclo-B-homopregnane derivatives with the corticoid ketol side chain
    1980, Vol. 45, Issue 1, pp. 269–273 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Acetolysis of 4β-methanesulphonyloxy-6β,7aβ-cyclo-B-homo-5α-cholestane
    1979, Vol. 44, Issue 11, pp. 3308–3320 [Abstract]
  • Pavel Kočovský and Václav Černý
    Synthesis of 6β,19-dimethoxy-3α,5-cyclo-5α-pregnan-20-one
    1979, Vol. 44, Issue 7, pp. 2275–2283 [Abstract]
  • Pavel Kočovský and Václav Černý
    Participation of 19-ester groups in the cleavage of 2α,3α- and 5α,6α-steroid epoxides. A case of competition between participation and external nucleophile attack
    1979, Vol. 44, Issue 5, pp. 1496–1509 [Abstract]
  • Pavel Kočovský, Václav Černý and Miroslava Synáčková
    Participation of 19-ester groups in hypobromous acid additions to 2,3- and 5,6-unsaturated steroids
    1979, Vol. 44, Issue 5, pp. 1483–1495 [Abstract]
  • Helena Velgová, Miroslava Synáčková and Václav Černý
    Preparation of some 3α,5-cycloandrostane derivatives with expanded ring B
    1979, Vol. 44, Issue 1, pp. 260–268 [Abstract]
  • Pavel Kočovský and Václav Černý
    Reduction of some mesyloxy and tosyloxy steroids with sodium iodide and zinc dust
    1979, Vol. 44, Issue 1, pp. 246–250 [Abstract]
  • Pavel Kočovský, Václav Černý and František Tureček
    Westphalen rearrangement. Mechanism of formation of 5α-acetoxy derivatives
    1979, Vol. 44, Issue 1, pp. 234–245 [Abstract]
  • Pavel Kočovský and Václav Černý
    Participation of the methoxyl group in the cleavage of some 19-substituted steroid epoxides. A case of competition between internal and external nucleophile attack
    1979, Vol. 44, Issue 1, pp. 226–233 [Abstract]
  • Bruno Schönecker, Dieter Tresselt, Gerd Schubert, Ladislav Kohout and Jan Fajkoš
    1H-NMR investigations. Application of trichloroacetyl isocyanate to structure determination of 3-, 6-, 7-, 7a- and 17-hydroxy steroids
    1978, Vol. 43, Issue 10, pp. 2609–2618 [Abstract]
  • Pavel Kočovský and Václav Černý
    Preparation of some 6β-substituted 5-hydroxy-5α-cholest-2-enes
    1978, Vol. 43, Issue 7, pp. 1933–1941 [Abstract]
  • Pavel Kočovský and Václav Černý
    Participation of the methoxyl group in electrophilic additions to some unsaturated 19-methoxy steroids
    1978, Vol. 43, Issue 7, pp. 1924–1932 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Methylenation of 4,6-cholestadien-3-one
    1978, Vol. 43, Issue 4, pp. 1134–1141 [Abstract]
  • Ladislav Kohout
    2,3-Disubstituted derivatives of the 6β,7aβ-cyclo-B-homo-5α-cholestane series
    1978, Vol. 43, Issue 3, pp. 889–899 [Abstract]
  • Ladislav Kohout and Jan Fajkoš
    Fission of the epimeric 2,3-epoxides in the 5,7β-cyclo-B-homo-5β-cholestane series
    1978, Vol. 43, Issue 2, pp. 638–646 [Abstract]
  • Pavel Kočovský and Václav Černý
    Neighboring group participation in some electrophilic additions to 19-substituted 5α-cholest-2-enes and 5-cholestenes
    1978, Vol. 43, Issue 1, pp. 327–335 [Abstract]