Collect. Czech. Chem. Commun. 1982, 47, 124-129
https://doi.org/10.1135/cccc19820124

Mechanism of acid cleavage of some steroid epoxides. Competition between neighboring group participation and external nucleophile attack

Pavel Kočovskýa, František Turečekb and Václav Černýa

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Jaroslav Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 121 38 Prague 2

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    2001, Vol. 66, Issue 7, pp. 1038–1046 [Abstract]
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    1988, Vol. 53, Issue 9, pp. 2140–2158 [Abstract]
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    1983, Vol. 48, Issue 12, pp. 3660–3673 [Abstract]
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    1983, Vol. 48, Issue 12, pp. 3618–3628 [Abstract]
  • Pavel Kočovský
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    1983, Vol. 48, Issue 12, pp. 3606–3617 [Abstract]
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    Synthesis of some unsaturated 19a-homocholestane derivatives
    1983, Vol. 48, Issue 12, pp. 3597–3605 [Abstract]
  • Pavel Kočovský
    Synthesis of some 2,3- and 5,6-unsaturated 19-homosteroids bearing an oxygen containing group at the position 19a
    1983, Vol. 48, Issue 12, pp. 3589–3596 [Abstract]
  • Pavel Kočovský, Ivo Starý, František Tureček and Vladimír Hanuš
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    1983, Vol. 48, Issue 10, pp. 2994–3019 [Abstract]
  • Karel Mach, Lidmila Petrusová, Helena Antropiusová, Vladimír Hanuš, František Tureček and Petr Sedmera
    Intermolecular hydrogen transfer in unsaturated hydrocarbons induced by dimeric titanocene
    1983, Vol. 48, Issue 10, pp. 2924–2936 [Abstract]
  • Václav Černý and Pavel Kočovský
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    1982, Vol. 47, Issue 11, pp. 3062–3076 [Abstract]
  • Miloslav Frumar, Gustáv Plesch, Eva Černošková, Václav Černý, Ladislav Tichý and Helena Tichá
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    1982, Vol. 47, Issue 7, pp. 1787–1793 [Abstract]
  • František Tureček
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    1982, Vol. 47, Issue 3, pp. 858–876 [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
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  • Pavel Kočovský, Pavel Drašar, Vladimír Pouzar and Miroslav Havel
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    1982, Vol. 47, Issue 1, pp. 108–116 [Abstract]
  • Vladimír Pouzar, Pavel Drašar, Pavel Kočovský and Miroslav Havel
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    1982, Vol. 47, Issue 1, pp. 96–107 [Abstract]
  • Pavel Drašar, František Tureček and Miroslav Havel
    17β-[4-(1,3-Thiazolyl)]-androst-5-ene derivatives
    1981, Vol. 46, Issue 11, pp. 2906–2911 [Abstract]
  • Pavel Kočovský
    Synthesis of 19-nor-10β-vinyl-5α-cholestane and its 5β-epimer
    1981, Vol. 46, Issue 11, pp. 2898–2905 [Abstract]
  • Pavel Kočovský and František Tureček
    An unusual rearrangement in hypobromous acid addition to 10β-vinyl cholestane derivatives
    1981, Vol. 46, Issue 11, pp. 2892–2897 [Abstract]
  • Pavel Kočovský and František Tureček
    Neighboring group participation and rearrangement in hypobromous acid addition to 10β-vinyl cholestane derivatives
    1981, Vol. 46, Issue 11, pp. 2877–2891 [Abstract]
  • František Tureček, Tomáš Trnka and Miloslav Černý
    Fragmentation of isomeric dideoxy derivatives of 1,6-anhydro-β-D-hexopyranoses under electron impact
    1981, Vol. 46, Issue 10, pp. 2390–2403 [Abstract]
  • František Tureček, Vladimír Hanuš, Petr Sedmera, Helena Antropiusová and Karel Mach
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    1981, Vol. 46, Issue 6, pp. 1474–1485 [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]
  • Pavel Kočovský
    Synthesis of 3,4-, 4,5- and 5,6-unsaturated 19-substituted cholestane derivatives and related epoxides
    1980, Vol. 45, Issue 11, pp. 3008–3022 [Abstract]
  • Pavel Kočovský
    Synthesis of 14-deoxy-14α-strophanthidin
    1980, Vol. 45, Issue 11, pp. 2998–3007 [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]
  • František Tureček
    Preparation of cycloheptanols symmetrically labelled with deuterium
    1980, Vol. 45, Issue 6, pp. 1820–1825 [Abstract]
  • Pavel Kočovský and Václav Černý
    Synthesis of 14-deoxy-14α-strophanthidol
    1980, Vol. 45, Issue 3, pp. 921–926 [Abstract]
  • Jan Fajkoš, Jiří Joska and František Tureček
    Solvolysis of 5,6β-cyclopropano-5β-cholestane-3β,19-diol 3-acetate 19-p-toluenesulphonate
    1980, Vol. 45, Issue 2, pp. 584–598 [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]
  • František Tureček and Pavel Kočovský
    The synthesis and mass spectra of some oxygen-bridged 5α-cholestane and B-homo-5α-cholestane derivatives
    1980, Vol. 45, Issue 1, pp. 274–293 [Abstract]
  • František Tureček, Vladimír Hanuš and Miloš Tichý
    The role of conformational mobility in the stereospecific loss of water under electron impact
    1979, Vol. 44, Issue 12, pp. 3595–3603 [Abstract]
  • František Tureček, Olga Turečková and Jaroslav Julák
    The syntheses of methyl esters of pentadeconic acids with double branched chain
    1979, Vol. 44, Issue 10, pp. 3111–3118 [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
    Model experiments in the synthetic approach to strophanthidin: The synthesis of 3β,5-dihydroxy-5β-cholestan-19-al
    1979, Vol. 44, Issue 7, pp. 2156–2160 [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]
  • František Tureček and Pavel Kočovský
    Mass spectra of some 5-methyl-19-nor-5β-cholest-9-enes
    1979, Vol. 44, Issue 2, pp. 429–438 [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]
  • Huynh Kim Thoa, Želimír Procházka, Miloš Buděšínský and Pavel Kočovský
    Hydroxylation of 6β-methoxy-3α,5-cyclo-5α-androstan-17-one with Rhizopus nigricans
    1978, Vol. 43, Issue 9, pp. 2305–2311 [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]
  • 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]