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

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

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ANTONCHICK, 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. 2(9), pp. 735-740. ISSN 1755-4330. eISSN 1755-4349. Available under: doi: 10.1038/nchem.730

@article{Antonchick2010-09Highl-42489, title={Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products}, year={2010}, doi={10.1038/nchem.730}, 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} }

Rauh, Daniel eng Rauh, Daniel 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 CuPF<sub>6</sub>(CH<sub>3</sub>CN)<sub>4</sub>. 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. Antonchick, Andrey P. Schürmann, Markus Antonchick, Andrey P. Catarinella, Mario Ziegler, Slava Waldmann, Herbert Waldmann, Herbert Gerding-Reimers, Claas 2010-09 Preut, Hans Schürmann, Markus Ziegler, Slava Gerding-Reimers, Claas 2018-06-04T07:51:37Z 2018-06-04T07:51:37Z Catarinella, Mario Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products Preut, Hans

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