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2015 | 2 | 1 |
Tytuł artykułu

One-pot synthesis of(R)-convolutamydineA involvingin situchiral organocatalyst formation

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The application of a convenient one-pot synthetic strategy, utilizing an in situ formed organocatalyst, to the enantioselective synthesis of anti-leukaemia agent (R)-convolutamydine A has been demonstrated.
Wydawca

Rocznik
Tom
2
Numer
1
Opis fizyczny
Daty
otrzymano
2014-10-20
zaakceptowano
2014-10-29
online
2015-01-12
Twórcy
autor
  • Department of Chemistry and
    Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for
    Molecular Materials, University of Erlangen-Nürnberg, Henkestraße
    42, 91054, Erlangen, Germany
  • Department of Chemistry and
    Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for
    Molecular Materials, University of Erlangen-Nürnberg, Henkestraße
    42, 91054, Erlangen, Germany
  • Institute of Chemistry, Academy
    of Sciences of Moldova, Academy Str. 3, MD-2028 Chisinau,
    Moldova
  • Institute of Chemistry, Academy
    of Sciences of Moldova, Academy Str. 3, MD-2028 Chisinau,
    Moldova
autor
1
  • Department of Chemistry and
    Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for
    Molecular Materials, University of Erlangen-Nürnberg, Henkestraße
    42, 91054, Erlangen, Germany
  • Department of Chemistry, Loughborough University,
    Loughborough LE11 3TU, UK
  • Department of Chemistry and
    Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for
    Molecular Materials, University of Erlangen-Nürnberg, Henkestraße
    42, 91054, Erlangen, Germany
Bibliografia
  • [1] Nicolaou, K.C., Montagnon, T., Snyder, S.A., Tandem reactions,cascade sequences, and biomimetic strategies in totalsynthesis, Chem. Commun., 2003, 551-564.[Crossref]
  • [2] Tietze, L.F., Brasche, G., Gericke, K. M., Domino Reactions inOrganic Synthesis, Wiley-VCH, Weinheim, 2006.
  • [3] Tietze, L. F., Domino Reactions: Concepts for Efficient OrganicSynthesis, Wiley-VCH, Weinheim, 2014.
  • [4] Nicolaou, K.C., Edmonds, D.J., Bulger, P. G., Cascade Reactionsin Total Synthesis, Angew. Chem. Int. Ed., 2006, 45, 7134-7186.[Crossref]
  • [5] Enders, D., Grondal, C., Hüttl, M.R.M., Asymmetric OrganocatalyticDomino Reactions, Angew. Chem. Int. Ed., 2007, 46,1570-1581.[Crossref]
  • [6] Vaxelaire, C., Winter, P., Christmann, M., One-Pot ReactionsAccelerate the Synthesis of Active Pharmaceutical Ingredients,Angew. Chem. Int. Ed., 2011, 50, 3605-3607.[Crossref][WoS]
  • [7] Albrecht, Ł., Jiang, H., Jørgensen, K. A., A Simple Recipe forSophisticated Cocktails: Organocatalytic One-Pot Reactions-Concept, Nomenclature, and Future Perspectives, Angew.Chem. Int. Ed., 2011, 50, 8492-8509 and references therein.[WoS][Crossref]
  • [8] Weiß, K., Wei, S.-W., Tsogoeva, S. B., Novel one-pot process forthe synthesis of 1,3-thiazoles via organocatalysed epoxidationof nitro-olefins, Org. Biomol. Chem., 2011, 9, 3457-3461.[WoS][Crossref]
  • [9] Wei, S.-W., Weiß, K. M., Tsogoeva, S. B., Convenient One-PotTwo-Step Synthesis of 1,3-Thiazoles via OrganocatalyzedEpoxidation of Nitroolefins, Synthesis, 2012, 44, 3441-3446.[WoS]
  • [10] Ibrahim, M. M.; Grau, D., Hampel, F., Tsogoeva,S.B., α-NitroEpoxides in Organic Synthesis: Development of a One-PotOrganocatalytic Strategy for the Synthesis of Quinoxalines, Eur.J. Org. Chem., 2014, 1401-1405.[Crossref]
  • [11] Wei, S.-W., Messerer, R., Tsogoeva, S.B., Asymmetric Synthesisof β-Adrenergic Blockers through Multistep One-Pot TransformationsInvolving In Situ Chiral Organocatalyst Formation,Chem. Eur. J., 2011, 17, 14380-14384.[WoS][Crossref]
  • [12] Kamano, Y., Zang, H., Ichihara, Y., Kizu, H., Komiyama,K., Pettit, G.R., Convolutamydine A, a novel bioactivehydroxyoxindole alkaloid from marine bryozoan Amathiaconvoluta, Tetrahedron Lett., 1995, 36, 2783-2784.[Crossref]
  • [13] Luppi, G., Monari, M., Corrêa, R. J., Violante, F. de A., Pinto, A.C., Kaptein, B., Broxterman, Q. B., Garden, S. J., Tomasini, C.,The first total synthesis of (R)-convolutamydine A, Tetrahedron,2006, 62, 12017-12024.[Crossref]
  • [14] Chen, J.-R., Liu, X.-P., Zhu, X.-Y., Li, L., Qiao, Y.-F., Xiao, W.-J.,Zhang, J.-M. Organocatalytic asymmetric aldol reaction ofketones with isatins: straightforward stereoselective synthesisof 3-alkyl-3-hydroxyindolin-2-ones, Tetrahedron, 2007, 63,10437-10444.[WoS][Crossref]
  • [15] Malkov, A.V., Kabeshov, M. A., Bella, M., Kysilka, O., Malyshev,D.A., Pluháčková, K., Kočovský, P., Vicinal Amino Alcoholsas Organocatalysts in Asymmetric Cross-Aldol Reaction ofKetones: Application in the Synthesis of Convolutamydine A,Org. Lett., 2007, 9, 5473-5476.
  • [16] Nakamura, S., Hara, N., Nakashima, H., Kubo, K., Shibata, N.,Toru, T., Enantioselective Synthesis of (R)-Convolutamydine Awith New N-Heteroarylsulfonylprolinamides, Chem. Eur. J.,2008, 14, 8079-8081.[WoS][Crossref]
  • [17] Held, F. E., Wei, S., Eder, K., Tsogoeva, S. B., One-pot route toβ-adrenergic blockers via enantioselective organocatalysedepoxidation of terminal alkenes as a key step, RSC Adv., 2014,4, 32796-32801.[WoS]
  • [18] Tsogoeva, S. B., Wei, S.-W., (S)-Histidine-based dipeptidesas organic catalysts for direct asymmetric aldol reactions,Tetrahedron: Asymmetry, 2005, 16, 1947-1951.[Crossref][WoS]
  • [19] Tsogoeva, S. B., Jagtap, S. B., Ardemasova, Z. A.,4-trans-Amino-proline based di- and tetrapeptides as organiccatalysts for asymmetric C-C bond formation reactions,Tetrahedron: Asymmetry, 2006, 17, 989-992.[Crossref]
  • [20] Baudequin, C., Zamfir, A., Tsogoeva, S. B., Highly enantioselectiveorganocatalytic formation of a quaternary carbon centervia chiral Brønsted acid catalyzed self-coupling of enamides,Chem. Commun., 2008, 4637-4639.[Crossref]
  • [21] Freund, M. H., Tsogoeva, S. B., L-Proline-Catalyzed AsymmetricMichael Addition of 2-Oxindoles to Enones: A Convenient Access to Oxindoles with a Quaternary Stereocenter, Synlett,2011, 503-507.[WoS]
  • [22] Reiter, C., López, S., Schmid, B., Neiss, C., Görling, A.,Tsogoeva. S. B., Michael Addition of N-Unprotected2-Oxindoles to Nitrostyrene Catalyzed by Bifunctional TertiaryAmines: Crucial Role of Dispersion Interactions, ChemCatChem,2014, 6, 1324-1332.[WoS]
  • [23] Messerer M., Wennemers H., Reversing the enantioselectivityof a peptidic catalyst by changing the solvent, Synlett, 2011,499-502.[WoS]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_asorg-2014-0002
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