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Collect. Czech. Chem. Commun. 2005, 70, 1447-1464
https://doi.org/10.1135/cccc20051447

Preparation of New Oxidized 18-α-Oleanane Derivatives

Miroslav Kvasnicaa, Iva Tišlerováa, Jan Šareka,*, Jan Sejbala and Ivana Císařováb

a Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague 2, Czech Republic
b Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Prague 2, Czech Republic

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  • Krainova Gulnaz, Beloglazova Yulia, Dmitriev Maksim, Grishko Victoria: Stereoselective Epoxidation of Triterpenic Allylic Alcohols and Cytotoxicity Evaluation of Synthesized Compounds. Molecules 2023, 28, 550. <https://doi.org/10.3390/molecules28020550>
  • Yaremenko Ivan A., Belyakova Yulia Yu., Radulov Peter S., Novikov Roman A., Medvedev Michael G., Krivoshchapov Nikolai V., Korlyukov Alexander A., Alabugin Igor V., Terent′ev Alexander O.: Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities. J. Am. Chem. Soc. 2022, 144, 7264. <https://doi.org/10.1021/jacs.2c00406>
  • Pakulski Zbigniew, Cmoch Piotr, Korda Anna, Luboradzki Roman, Gwardiak Katarzyna, Karczewski Romuald: Rearrangements of the Betulin Core. Synthesis of Terpenoids Possessing the Bicyclo[3.3.1]nonane Fragment by Rearrangement of Lupane-Type Epoxides. J. Org. Chem. 2021, 86, 1084. <https://doi.org/10.1021/acs.joc.0c02560>
  • Yaremenko Ivan A., Belyakova Yulia Yu., Radulov Peter S., Novikov Roman A., Medvedev Michael G., Krivoshchapov Nikolai V., Korlyukov Alexander A., Alabugin Igor V., Terent’ev Alexander O.: Marriage of Peroxides and Nitrogen Heterocycles: Selective Three-Component Assembly, Peroxide-Preserving Rearrangement, and Stereoelectronic Source of Unusual Stability of Bridged Azaozonides. J. Am. Chem. Soc. 2021, 143, 6634. <https://doi.org/10.1021/jacs.1c02249>
  • Yaremenko Ivan A., Radulov Peter S., Belyakova Yulia Y., Demina Arina A., Fomenkov Dmitriy I., Barsukov Denis V., Subbotina Irina R., Fleury Fabrice, Terent'ev Alexander O.: Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application. Chemistry A European J 2020, 26, 4734. <https://doi.org/10.1002/chem.201904555>
  • Kazakova Oxana B., Khusnutdinova Elmira F., Petrova Anastasiya V., Yamansarov Emil Yu., Lobov Alexander N., Fedorova Alexandra A., Suponitsky Kyrill Yu.: Diastereoselective Synthesis of Triterpenoid 1,2,4-Trioxolanes by Griesbaum Co-ozonolysis. J. Nat. Prod. 2019, 82, 2550. <https://doi.org/10.1021/acs.jnatprod.9b00393>
  • Tolmacheva Irina A., Nazarov Alexey V., Eroshenko Daria V., Grishko Victoria V.: Synthesis, cytotoxic evaluation, and molecular docking studies of the semi-synthetic “triterpenoid-steroid” hybrids. Steroids 2018, 140, 131. <https://doi.org/10.1016/j.steroids.2018.10.005>
  • Yaremenko Ivan A., Gomes Gabriel dos Passos, Radulov Peter S., Belyakova Yulia Yu., Vilikotskiy Anatoliy E., Vil’ Vera A., Korlyukov Alexander A., Nikishin Gennady I., Alabugin Igor V., Terent’ev Alexander O.: Ozone-Free Synthesis of Ozonides: Assembling Bicyclic Structures from 1,5-Diketones and Hydrogen Peroxide. J. Org. Chem. 2018, 83, 4402. <https://doi.org/10.1021/acs.joc.8b00130>
  • dos Passos Gomes Gabriel, Yaremenko Ivan A., Radulov Peter S., Novikov Roman A., Chernyshev Vladimir V., Korlyukov Alexander A., Nikishin Gennady I., Alabugin Igor V., Terent'ev Alexander O.: Stereoelectronic Control in the Ozone‐Free Synthesis of Ozonides. Angewandte Chemie 2017, 129, 5037. <https://doi.org/10.1002/ange.201610699>
  • dos Passos Gomes Gabriel, Yaremenko Ivan A., Radulov Peter S., Novikov Roman A., Chernyshev Vladimir V., Korlyukov Alexander A., Nikishin Gennady I., Alabugin Igor V., Terent'ev Alexander O.: Stereoelectronic Control in the Ozone‐Free Synthesis of Ozonides. Angew Chem Int Ed 2017, 56, 4955. <https://doi.org/10.1002/anie.201610699>
  • Tolmacheva Irina A., Nazarov Alexey V., Dmitriev Maxim V., Boreko Eugene I., Grishko Victoria V.: Synthesis of 1,10-seco-triterpenoids by the Beckmann fragmentation from allobetulin. Tetrahedron 2017, 73, 6448. <https://doi.org/10.1016/j.tet.2017.09.044>
  • Grishko V. V., Tolmacheva I. A., Pereslavtseva A. V.: Triterpenoids with a Five-Membered a-Ring: Distribution in Nature, Transformations, Synthesis, and Biological Activity. Chem Nat Compd 2015, 51, 1. <https://doi.org/10.1007/s10600-015-1193-z>
  • Chaudhary Sandeep, Sharma Vashundhra, Jaiswal Pradeep K., Gaikwad Anil N., Sinha Sudhir K., Puri Sunil K., Sharon Ashoke, Maulik Prakas R., Chaturvedi Vinita: Stable Tricyclic Antitubercular Ozonides Derived from Artemisinin. Org. Lett. 2015, 17, 4948. <https://doi.org/10.1021/acs.orglett.5b02296>
  • Kvasnica Miroslav, Urban Milan, Dickinson Niall J., Sarek Jan: Pentacyclic triterpenoids with nitrogen- and sulfur-containing heterocycles: synthesis and medicinal significance. Nat. Prod. Rep. 2015, 32, 1303. <https://doi.org/10.1039/C5NP00015G>
  • Pereslavtseva A. V., Tolmacheva I. A., Slepukhin P. A., El’tsov O. S., Kucherov I. I., Eremin V. F., Grishko V. V.: Synthesis of A-Pentacyclic Triterpene α,β-Alkenenitriles. Chem Nat Compd 2014, 49, 1059. <https://doi.org/10.1007/s10600-014-0822-2>
  • Kazakova O. B., Smirnova I. E., Khusnutdinova E. F., Zhukova O. S., Fetisova L. V., Apryshko G. N., Medvedeva N. I., Yamansarov E. Yu., Baikova I. P., Nguyen Thanh Tra, Thu H. Do Thi: Synthesis and cytotoxicity of allobetulin derivatives. Russ J Bioorg Chem 2014, 40, 558. <https://doi.org/10.1134/S1068162014050082>
  • Shernyukov A. V., Salakhutdinov N. F., Tolstikov G. A.: Methods of the synthesis of A-seco derivatives of pentacyclic triterpenoids. Russ Chem Bull 2013, 62, 878. <https://doi.org/10.1007/s11172-013-0120-3>
  • Kvasnica Miroslav, Rudovska Iva, Hajduch Marian, Sarek Jan: Preparation of new 18α-oleanane alcohols: synthesis, characterization, and cytotoxic activity. Monatsh Chem 2010, 141, 233. <https://doi.org/10.1007/s00706-009-0249-9>
  • Salvador Jorge A. R., Pinto Rui M. A., Santos Rita C., Le Roux Christophe, Beja Ana Matos, Paixão José A.: Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18α-oleanane core and A-neo-18α-oleanene compounds from lupanes. Org. Biomol. Chem. 2009, 7, 508. <https://doi.org/10.1039/B814448F>
  • Kvasnica Miroslav, Rudovska Iva, Cisarova Ivana, Sarek Jan: Reaction of lupane and oleanane triterpenoids with Lawesson's reagent. Tetrahedron 2008, 64, 3736. <https://doi.org/10.1016/j.tet.2008.02.023>
  • Urban Milan, Sarek Jan, Kvasnica Miroslav, Tislerova Iva, Hajduch Marian: Triterpenoid Pyrazines and Benzopyrazines with Cytotoxic Activity. J. Nat. Prod. 2007, 70, 526. <https://doi.org/10.1021/np060436d>
  • Kvasnica Miroslav, Tislerova Iva, Sarek Jan, Sejbal Jan, Cisarova Ivana: Preparation of New Oxidized 18‐α‐Oleanane Derivatives. ChemInform 2006, 37. <https://doi.org/10.1002/chin.200612189>
  • Medvedeva N. I., Flekhter O. B., Gzella A., Zaprutko L.: Structure of the minor ozonolysis product of 19β,28-epoxy-A-neo-18α-olean-3(5)-ene. Chem Nat Compd 2006, 42, 618. <https://doi.org/10.1007/s10600-006-0233-0>
  • Krasutsky Pavel A.: Birch bark research and development. Nat. Prod. Rep. 2006, 23, 919. <https://doi.org/10.1039/b606816b>