A ligand-directed divergent catalytic approach to establish structural and functional scaffold diversity

Yen-Chun Lee, Sumersing Patil, Christopher Golz, Carsten Strohmann, Slava Ziegler, Kamal Kumar () and Herbert Waldmann ()
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Yen-Chun Lee: Max-Planck-Institut für Molekulare Physiologie
Sumersing Patil: Max-Planck-Institut für Molekulare Physiologie
Christopher Golz: Technische Universität Dortmund, Fakultät Chemie, Chemische Biologie
Carsten Strohmann: Technische Universität Dortmund, Fakultät Chemie, Chemische Biologie
Slava Ziegler: Max-Planck-Institut für Molekulare Physiologie
Kamal Kumar: Max-Planck-Institut für Molekulare Physiologie
Herbert Waldmann: Max-Planck-Institut für Molekulare Physiologie

Nature Communications, 2017, vol. 8, issue 1, 1-12

Abstract: Abstract The selective transformation of different starting materials by different metal catalysts under individually optimized reaction conditions to structurally different intermediates and products is a powerful approach to generate diverse molecular scaffolds. In a more unified albeit synthetically challenging strategy, common starting materials would be exposed to a common metal catalysis, leading to a common intermediate and giving rise to different scaffolds by tuning the reactivity of the metal catalyst through different ligands. Herein we present a ligand-directed synthesis approach for the gold(I)-catalysed cycloisomerization of oxindole-derived 1,6-enynes that affords distinct molecular scaffolds following different catalytic reaction pathways. Varying electronic properties and the steric demand of the gold(I) ligands steers the fate of a common intermediary gold carbene to selectively form spirooxindoles, quinolones or df-oxindoles. Investigation of a synthesized compound collection in cell-based assays delivers structurally novel, selective modulators of the Hedgehog and Wnt signalling pathways, autophagy and of cellular proliferation.

Date: 2017
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DOI: 10.1038/ncomms14043

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