Collect. Czech. Chem. Commun. 1999, 64, 329-347
https://doi.org/10.1135/cccc19990329

Reaction of 18β,19β-Epoxylupan-21-one Derivatives with Acids: A Way to 21,22-Disubstituted Lup-18-ene Triterpenoids

Eva Klinotová*, Jitka Čermáková, Martin Rejzek, Václav Křeček, Jan Sejbal, Petr Olšovský and Jiří Klinot

Department of Organic Chemistry, Faculty of Science, Charles University, 128 40 Prague 2, Czech Republic

Individual author index pages


Other CCCC articles of these authors

  • Martin Dračínský, Simona Hybelbauerová, Jan Sejbal and Miloš Buděšínský*
    Preparation and Conformational Study of B-Ring Substituted Lupane Derivatives
    2006, Vol. 71, Issue 8, pp. 1131–1160 [Abstract]
  • Jiří Zedník*, Jan Sejbal, Jan Svoboda, Jan Sedláček and Jiří Vohlídal
    Structure Dynamics and Isomerism of Bis[μ-(2-methylphenolato)]bis[(η22-cycloocta-1,5-diene)rhodium(I)] Complex
    2006, Vol. 71, Issue 3, pp. 423–433 [Abstract]
  • Martin Dračínský, Václav Richtr, Václav Křeček, Jan Sejbal, Jiří Klinot and Miloš Buděšínský*
    Preparation and Conformational Study of 19β,28-Epoxy-18α-olean-5-ene Derivatives
    2006, Vol. 71, Issue 3, pp. 387–410 [Abstract]
  • Iva Tišlerová*, Václav Richtr and Jiří Klinot
    Conformation Study of A-Ring in 19β,28-Epoxy-2-fluoro-18α-oleananes
    2006, Vol. 71, Issue 3, pp. 368–386 [Abstract]
  • Irena Němcová*, Karel Nesměrák, Božena Kafková and Jan Sejbal
    Physicochemical Properties of 9-(Alkylsulfanyl)- and 9-(Arylsulfanyl)acridine Derivatives and Their Interaction with (2-Hydroxypropyl)cyclodextrins
    2006, Vol. 71, Issue 2, pp. 179–189 [Abstract]
  • Miroslav Kvasnica, Iva Tišlerová, Jan Šarek*, Jan Sejbal and Ivana Císařová
    Preparation of New Oxidized 18-α-Oleanane Derivatives
    2005, Vol. 70, Issue 9, pp. 1447–1464 [Abstract]
  • Iva Tišlerová*, Eva Klinotová, Jiří Klinot, Jan Sejbal, Martin Rejzek and Stanislav Hilgard
    Preparation of E-Secolupane Acids and Lactones
    2003, Vol. 68, Issue 4, pp. 751–778 [Abstract]
  • Jan Sejbal*, Martina Homolová, Iva Tišlerová and Václav Křeček
    Preparation and Conformational Analysis of 1,2-Seco Derivatives of 19β,28-Epoxy-18α-oleanane
    2000, Vol. 65, Issue 8, pp. 1339–1356 [Abstract]
  • Jan Sejbal, Jiří Klinot, Miloš Buděšínský and Jiří Protiva
    Functionalization of Lupane-3β,28-diyl Diacetate with Chromium(VI) Oxide. Part 2
    1997, Vol. 62, Issue 12, pp. 1905–1918 [Abstract]
  • Eva Klinotová, Václav Křeček, Jiří Klinot, Magdalena Endová, Jana Eisenreichová, Miloš Buděšínský and Martin Štícha
    Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series
    1997, Vol. 62, Issue 11, pp. 1776–1798 [Abstract]
  • Jiří Protiva, Thi Thu Huong Nguyen, Jiří Urban and Eva Klinotová
    Reactions of 21-Acetoxy-16α,17α-epoxypregn-4-ene-3,20-dione with Nitrogen-Containing Nucleophilic Agents
    1997, Vol. 62, Issue 7, pp. 1095–1104 [Abstract]
  • Thi Thu Huong Nguyen, Jiří Protiva, Eva Klinotová, Jiří Urban and Miroslav Protiva
    Synthesis of 24-(Piperidin-1-yl, Morpholin-4-yl and 4-Methylpiperazin-1-yl)-5β-cholan-3α-ols and Four Hydroxylated 23-(4,5-Dihydroimidazol-2-yl)-24-nor-5β-cholanes
    1997, Vol. 62, Issue 3, pp. 471–478 [Abstract]
  • Jan Sejbal, Jiří Klinot and Miloš Buděšínský
    Functionalization of Lupane with Chromium(VI) Oxide. A Remark on the Structure of Clerodone
    1996, Vol. 61, Issue 9, pp. 1371–1379 [Abstract]
  • Jan Sejbal, Jiří Klinot and Miloš Buděšínský
    Oleanane Triterpenoids Functionalized at C-25 and C-26
    1996, Vol. 61, Issue 9, pp. 1360–1370 [Abstract]
  • Tomáš Elbert, Martin Rejzek and Henri Virelizier
    Regioselective Tritiation of Carbamate Dicyclic Juvenoids
    1996, Vol. 61, Issue 6, pp. 946–950 [Abstract]
  • Martin Rejzek, Marie Zarevúcka, Zdeněk Wimmer, Tomáš Vaněk, Richard Tykva, Jelena Kuldová, David Šaman and Blanka Bennettová
    Synthesis of Juvenile Hormone Bioanalogs Derived from 2-(4-Hydroxybenzyl)-6-methylcyclohexanone
    1996, Vol. 61, Issue 4, pp. 605–614 [Abstract]
  • Václav Křeček, Stanislav Hilgard, Miloš Buděšínský and Alois Vystrčil
    E-Homolupane Derivatives Substituted in Position 17 and 22a. 1H NMR, 13C NMR and IR Spectra
    1995, Vol. 60, Issue 4, pp. 619–635 [Abstract]
  • Thi Thu Huong Nguyen, Jiří Urban, Eva Klinotová, Jan Sejbal, Jiří Protiva, Pavel Drašar and Miroslav Protiva
    Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds
    1995, Vol. 60, Issue 2, pp. 257–275 [Abstract]
  • Magdalena Endová, Eva Klinotová, Jan Sejbal, Bohumil Máca, Jiří Klinot and Jiří Protiva
    Preparation of 2,3-Secodiacids of the Lupane Series
    1994, Vol. 59, Issue 6, pp. 1420–1429 [Abstract]
  • Jiří Novotný, Jaroslav Podlaha and Jiří Klinot
    Crystal Structure and Conformation of Ring A of 2β-Bromo-19β,28-epoxy-18α-oleanan-3-one
    1993, Vol. 58, Issue 11, pp. 2737–2744 [Abstract]
  • Jiří Protiva, Václav Křeček, Luděk Vlk, Hana Malinová, Eva Klinotová, Bohumil Máca and Jiří Urban
    Indirect Iodination of Estrogenes via Triazenes
    1993, Vol. 58, Issue 11, pp. 2729–2736 [Abstract]
  • Eva Klinotová, Martin Rejzek, Hana Zůnová, Jan Sejbal, Jiří Klinot and Jiří Urban
    Oxidation of 3β,28-Diacetoxy-18-lupen-21-one with Peroxy Acids: A Way to Des-E-lupane Derivatives
    1993, Vol. 58, Issue 10, pp. 2505–2516 [Abstract]
  • Eva Klinotová, Jiří Klinot, Václav Křeček, Stanislav Hilgard, Miloš Buděšínský and Jan Malát
    Structure of Dimeric Compounds Obtained from 3β-Acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide
    1993, Vol. 58, Issue 7, pp. 1675–1691 [Abstract]
  • Eva Klinotová, Jiří Klinot, Václav Křeček, Miloš Buděšínský and Bohumil Máca
    21,22-Disubstituted 18α,19βH-Ursane Derivatives with Oxabicyclooctane System in Ring E
    1993, Vol. 58, Issue 1, pp. 173–190 [Abstract]
  • Václav Křeček, Miloš Buděšínský and Alois Vystrčil
    Preparation of 20R and 20S Acetylamino-30-norlupane Derivatives
    1992, Vol. 57, Issue 3, pp. 556–564 [Abstract]
  • Jan Sejbal, Jiří Klinot, Miloš Buděšínský and Jiří Protiva
    Functionalization of 3β,28-lupanediol diacetate with chromium(VI) oxide
    1991, Vol. 56, Issue 12, pp. 2936–2949 [Abstract]
  • Eva Klinotová, Václav Křeček, Jiří Klinot, Miloš Buděšínský, Jaroslav Podlaha, Jana Podlahová and Jiří Ječný
    An unusual reaction of a bridged triterpenoid α-diketone with acetic anhydride
    1991, Vol. 56, Issue 12, pp. 2917–2935 [Abstract]
  • Jan Sejbal, Jiří Klinot and Miloš Buděšínský
    Photolyses and pyrolyses of triterpenoid nitrites
    1991, Vol. 56, Issue 8, pp. 1732–1743 [Abstract]
  • Jiří Klinot, Stanislav Hilgard, Jakub Krijt and Petr Olšovský
    Infrared spectra of 2α-substituted 3-oxotriterpenoids and conformation of ring A
    1991, Vol. 56, Issue 5, pp. 966–972 [Abstract]
  • Alois Vystrčil, Václav Křeček, Jiří Protiva and Miloš Buděšínský
    Anhydrobetulin and its derivatives
    1991, Vol. 56, Issue 4, pp. 886–904 [Abstract]
  • Jiří Klinot, Miloš Buděšínský and Jarmil Světlý
    Conformation of ring A in triterpenoid and 4,4-dimethylsteroid 3-ketones. Chemical shifts of methyl protons and lanthanide and benzene induced shifts
    1990, Vol. 55, Issue 3, pp. 766–781 [Abstract]
  • Miloš Buděšínský and Jiří Klinot
    Conformation of ring A in triterpenoid ketones. Carbon-13 chemical shifts and spin-lattice relaxation times of lupane and 18α-oleanane derivatives
    1989, Vol. 54, Issue 7, pp. 1928–1939 [Abstract]
  • Jan Sejbal, Eva Klinotová, Markéta Bludská, Jiří Klinot and Miloš Buděšínský
    Conversion of betulin into careyagenolide (2α,3β-dihydroxy-18α,19βH-ursan-28,20β-olide)
    1989, Vol. 54, Issue 4, pp. 1036–1042 [Abstract]
  • Jiří Protiva, Václav Křeček, Bohumil Máca, Jiří Urban, Miloš Buděšínský and Miloš Procházka
    Synthesis of 4-(N-acetyl-L-tyrosyl)amino-2-iodobenzoic acid
    1989, Vol. 54, Issue 4, pp. 1012–1018 [Abstract]
  • Jiří Klinot, Jaroslav Podlaha, Jana Podlahová, Stanislav Hilgard and Eva Klinotová
    Conformation of ring A of 19β,28-epoxy-18α-oleanan-3-one in solution and in the solid state. Crystal structure and carbon-deuterium stretching frequencies
    1989, Vol. 54, Issue 3, pp. 737–750 [Abstract]
  • Jiří Klinot, Jaroslav Podlaha, Jana Podlahová, Karel Malý and Václav Petříček
    Conformation of ring A in 3-oxotriterpenoids. sofa conformation in 3-oxolupane-28-nitrile crystal
    1989, Vol. 54, Issue 3, pp. 725–736 [Abstract]
  • Jiří Klinot, Jiří Liška, Alena Forgáčová, Miloš Buděšínský, Jiří Protiva, Stanislav Hilgard and Alois Vystrčil
    Acid-catalyzed rearrangements of an A(1)-nor-triterpenoid 2α,3α-epoxide
    1989, Vol. 54, Issue 2, pp. 413–429 [Abstract]
  • Jiří Klinot, Jan Sejbal and Alois Vystrčil
    Triterpenoid 2,3-ketols, diols and their acetates: Preparation and conformation of the ring A
    1989, Vol. 54, Issue 2, pp. 400–412 [Abstract]
  • Jan Sejbal, Jiří Klinot and Alois Vystrčil
    Photolysis of 19β,28-epoxy-18α-oleanan-2β-ol nitrites: Functionalization of 10β- and 8β-methyl groups
    1988, Vol. 53, Issue 1, pp. 118–131 [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]
  • Jiří Protiva, Václav Křeček, Ladislav Lešetický and Petr Sedmera
    New intermediate for rapid synthesis of N-isopropyl-2-amino-1-(4-iodophenyl)propane (N-isopropyl-4-iodoamphetamine), labelled with radioactive iodine
    1987, Vol. 52, Issue 9, pp. 2274–2280 [Abstract]
  • Jan Sejbal, Jiří Klinot and Alois Vystrčil
    Reaction of 3-keto and 2-ketotriterpenoids with 3-chloroperoxybenzoic acid in aliphatic alcohols. A new method of preparation of α-hydroxy ketones
    1987, Vol. 52, Issue 4, pp. 1052–1061 [Abstract]
  • Jiří Protiva, Rudolf Očadlík, Eva Klinotová, Jiří Klinot and Alois Vystrčil
    Ethylene dithioketals in ring a of 19β,28-epoxy-18α-oleanane; Mass spectra and reduction with deuterated Raney-nickel
    1987, Vol. 52, Issue 2, pp. 501–507 [Abstract]
  • Jiří Klinot, Jiří Rozen, Eva Klinotová and Alois Vystrčil
    A-nor-derivatives of 19β,28-epoxy-18α-oleanane: Preparation and stereochemistry
    1987, Vol. 52, Issue 2, pp. 493–500 [Abstract]
  • Jan Sejbal, Jiří Klinot and Alois Vystrčil
    Oxidation of 3β,28-lupanediol diacetate and lupane with peroxyacetic acid
    1987, Vol. 52, Issue 2, pp. 487–492 [Abstract]
  • Jiří Klinot, Jarmil Světlý, Eva Klinotová, Miloš Buděšínský and Alois Vystrčil
    Preparation of isomeric 2-methyl-1-oxotriterpenoids of the 18α-oleanane series; Conformation of ring A
    1986, Vol. 51, Issue 12, pp. 2869–2878 [Abstract]
  • Jiří Protiva, Eva Klinotová, Jiří Klinot, Miroslav Kušiak and Alois Vystrčil
    Reduction of triterpenoid ketones by chloroiridic acid and trimethyl phosphite
    1986, Vol. 51, Issue 9, pp. 2029–2033 [Abstract]
  • Jiří Klinot, Milan Jirsa, Eva Klinotová, Karel Ubik and Jiří Protiva
    Isolation of (23R) 3α, 7α,23-trihydroxy-5β-cholan-24-oic (β-phocaecholic) acid from duck bile. 1H NMR spectra of its derivatives
    1986, Vol. 51, Issue 8, pp. 1722–1730 [Abstract]
  • Jiří Protiva, Jaroslav Pecka, Eva Klinotová and Miloš Procházka
    Synthesis of 16-(4-iodophenyl)hexadecanoic acid
    1986, Vol. 51, Issue 4, pp. 872–878 [Abstract]
  • Václav Křeček, Jiří Protiva, Miloš Buděšínský, Eva Klinotová and Alois Vystrčil
    Preparation of C(18)-empiric 20,29,30-trinorlupane derivatives. 1H, 13C NMR and mass spectra
    1986, Vol. 51, Issue 3, pp. 621–635 [Abstract]
  • Jiří Klinot, Václav Všetečka, Eva Klinotová and Alois Vystrčil
    Conformation of ring A in 3-oxotriterpenoids. Dipole moments and CD spectra
    1986, Vol. 51, Issue 3, pp. 611–620 [Abstract]
  • Jiří Klinot, Miloš Buděšínský, Eva Klinotová and Alois Vystrčil
    Conformation of the A ring in 1-oxo and 3-oxotriterpenoids. Vicinal interproton coupling constants
    1986, Vol. 51, Issue 3, pp. 593–610 [Abstract]
  • Alois Vystrčil, Václav Křeček, Miloš Buděšínský and Jiří Protiva
    Isomeric oximes of 30-norlupan-20-one and its derivatives
    1986, Vol. 51, Issue 3, pp. 581–592 [Abstract]
  • Jan Sejbal, Jiří Klinot, Jiří Protiva and Alois Vystrčil
    Reactions of triterpenoid ketones with sulfur and morpholine under the conditions of Willgerodt-Kindler reaction
    1986, Vol. 51, Issue 1, pp. 118–127 [Abstract]
  • Jiří Klinot, Jarmil Světlý, Eva Klinotová and Alois Vystrčil
    Preparation of isomeric 2-methyl-3-oxolupane-28-nitriles
    1985, Vol. 50, Issue 12, pp. 2918–2924 [Abstract]
  • Jan Sejbal, Jiří Klinot, Daniela Hrnčířová and Alois Vystrčil
    Oxidation of 19β,28-epoxy-18α-oleanan-3-one and -1-one with peracids
    1985, Vol. 50, Issue 12, pp. 2753–2759 [Abstract]
  • Eva Klinotová, Jiří Protiva, Jiří Klinot and Alois Vystrčil
    Reaction of 30-nor-18-lupene derivatives with bromine and peracids
    1984, Vol. 49, Issue 1, pp. 141–149 [Abstract]
  • Eva Klinotová, Jiří Klinot, Jiří Protiva, Jiří Urban and Alois Vystrčil
    Reaction of 30-nor-19(20)-lupene derivatives with bromine
    1983, Vol. 48, Issue 12, pp. 3444–3454 [Abstract]
  • Ján Galoci, Miloš Procházka and Eva Klinotová
    Pyrolysis of 2-acetoxycarboxylic acids
    1983, Vol. 48, Issue 6, pp. 1729–1733 [Abstract]
  • Alois Vystrčil, Václav Křeček and Miloš Buděšínský
    Elimination reaction of angular hydroxymethyl groups of 20(29)-lupene derivatives
    1983, Vol. 48, Issue 5, pp. 1499–1507 [Abstract]
  • Jiří Protiva, Václav Křeček, Josefa Křečková, Eva Klinotová and Alois Vystrčil
    The synthesis and the mass spectra of 28,29,30-trinoroleanane derivatives with a double bond in the ring E or D
    1983, Vol. 48, Issue 3, pp. 928–936 [Abstract]
  • Irena Valterová, Jiří Klinot and Alois Vystrčil
    Preparation and antibacterial activity of di-, tri- and tetraoic acids derived from 3,4-secolupane
    1983, Vol. 48, Issue 2, pp. 649–661 [Abstract]
  • Jiří Protiva, Luděk Lepša, Eva Klinotová, Jiří Klinot, Václav Křeček and Alois Vystrčil
    Homogeneous hydrogenation and deuteration of pentacyclic triterpenoids: Double bonds in side-chains
    1981, Vol. 46, Issue 11, pp. 2734–2741 [Abstract]
  • Jiří Protiva, Eva Klinotová, Hana Skorkovská and Alois Vystrčil
    Mass spectra of 18α,19βH-ursane derivatives with a lactone arrangement of the ring E
    1981, Vol. 46, Issue 4, pp. 1023–1030 [Abstract]
  • Eva Klinotová, Hana Skorkovská, Jiří Protiva, Jiří Urban and Alois Vystrčil
    Isomerization of ketolactone of oxabicyclo[2.2.2]octane pattern in the E ring of ursane derivatives
    1980, Vol. 45, Issue 8, pp. 2351–2359 [Abstract]
  • Irena Valterová, Jiří Klinot and Alois Vystrčil
    3,4-Seco-3,28-lupanedioic acids substituted in the side chain at C(5)
    1980, Vol. 45, Issue 7, pp. 1964–1973 [Abstract]
  • Eva Klinotová, Hana Skorkovská, Jiří Protiva and Alois Vystrčil
    Structure and the properties of 18α,19βH-ursane derivatives with a lactone bridge to ring E
    1980, Vol. 45, Issue 5, pp. 1366–1378 [Abstract]
  • Jiří Klinot, Jarmil Světlý, Dagmar Kudláčková, Miloš Buděšínský and Alois Vystrčil
    Preparation of 2-methyl-3-oxo triterpenoids of 18α-oleanane series and the conformation of ring A
    1979, Vol. 44, Issue 1, pp. 211–225 [Abstract]
  • Eva Klinotová, Stanislav Bosák and Alois Vystrčil
    The preparation of 19αH-lupeol acetate and its derivatives
    1978, Vol. 43, Issue 8, pp. 2204–2216 [Abstract]