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Spirocyclisation of phytoalexin 1-methoxybrassinin in the presence of Grignard reagents

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Abstract

The anti-cancer properties of naturally occurring (2R, 3R)-(−)-1-methoxyspirobrassinol methyl ether (I) and their synthetic amino or piperidyl analogues II inspired us to study the synthesis of new target compounds III with a C—C bond in the 2-position of indole rather than a C—N or C—O bond (I or II respectively). The goal was achieved via electrophilic-nucleophilic 3,2-difunctionalisation of 1-methoxybrassinin (IV) in the presence of bromine and the Grignard reagent leading to the formation of cis- and trans-C—C analogues of I. Finally, the anti-cancer activities of the new compounds were measured and compared with I and II in order to show the importance of a heteroatom in the 2-substituted indole on the anti-cancer activity of spirobrassinols.

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Authors and Affiliations

  1. Department of Organic Chemistry, Institute of Chemical Science, Faculty of Science, P. J. Šafárik University, Moyzesova 11, 040 01, Košice, Slovakia

    Peter Očenáš, Lucia Tomášová & Peter Kutschy

  2. Centre for Syntheses under Sustainable Conditions and their Management, Department of Chemistry, Masaryk University, Kotlářská 2, 611 37, Brno, Czech Republic

    Pavel Pazdera

  3. Department of Pharmacology, Faculty of Medicine, P. J. Šafárik University, SNP 1, 040 66, Košice, Slovakia

    Ján Mojžiš & Martina Pilátová

Authors
  1. Peter Očenáš
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  2. Lucia Tomášová
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  3. Peter Kutschy
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  4. Pavel Pazdera
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  5. Ján Mojžiš
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  6. Martina Pilátová
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Correspondence to Peter Očenáš.

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Očenáš, P., Tomášová, L., Kutschy, P. et al. Spirocyclisation of phytoalexin 1-methoxybrassinin in the presence of Grignard reagents. Chem. Pap. 67, 631–642 (2013). https://doi.org/10.2478/s11696-013-0335-7

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  • DOI: https://doi.org/10.2478/s11696-013-0335-7

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