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Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products

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2010

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Antonchick, Andrey P.
Gerding-Reimers, Claas
Schürmann, Markus
Preut, Hans
Ziegler, Slava
Rauh, Daniel
Waldmann, Herbert

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https://doi.org/10.1038/nchem.730
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Nature chemistry. 2010, 2(9), pp. 735-740. ISSN 1755-4330. eISSN 1755-4349. Available under: doi: 10.1038/nchem.730

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In biology-oriented synthesis the underlying scaffold classes of natural products selected in evolution are used to define biologically relevant starting points in chemical structure space for the synthesis of compound collections with focused structural diversity. Here we describe a highly enantioselective synthesis of natural-product-inspired 3,3'-pyrrolidinyl spirooxindoles--which contain an all-carbon quaternary centre and three tertiary stereocentres. This synthesis takes place by means of an asymmetric Lewis acid-catalysed 1,3-dipolar cycloaddition of an azomethine ylide to a substituted 3-methylene-2-oxindole using 1-3 mol% of a chiral catalyst formed from a N,P-ferrocenyl ligand and CuPF6(CH3CN)4. Cellular evaluation has identified a molecule that arrests mitosis, induces multiple microtubule organizing centres and multipolar spindles, causes chromosome congression defects during mitosis and inhibits tubulin regrowth in cells. Our findings support the concept that compound collections based on natural-product-inspired scaffolds constructed with complex stereochemistry will be a rich source of compounds with diverse bioactivity.

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570 Biowissenschaften, Biologie

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ISO 690ANTONCHICK, Andrey P., Claas GERDING-REIMERS, Mario CATARINELLA, Markus SCHÜRMANN, Hans PREUT, Slava ZIEGLER, Daniel RAUH, Herbert WALDMANN, 2010. Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products. In: Nature chemistry. 2010, 2(9), pp. 735-740. ISSN 1755-4330. eISSN 1755-4349. Available under: doi: 10.1038/nchem.730
BibTex
@article{Antonchick2010-09Highl-42489,
  year={2010},
  doi={10.1038/nchem.730},
  title={Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products},
  number={9},
  volume={2},
  issn={1755-4330},
  journal={Nature chemistry},
  pages={735--740},
  author={Antonchick, Andrey P. and Gerding-Reimers, Claas and Catarinella, Mario and Schürmann, Markus and Preut, Hans and Ziegler, Slava and Rauh, Daniel and Waldmann, Herbert}
}
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