Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

Mohammad Rehan; Jana Flegel; Franziska Heitkamp; Jorgelina L. Pergomet; Felix Otte; Carsten Strohmann; Kamal Kumar

doi:10.1055/s-0040-1707222

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(21): 3140-3152
DOI: 10.1055/s-0040-1707222

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Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators

Mohammad Rehan

^aMax-Planck-Institute für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany

,

Jana Flegel

^aMax-Planck-Institute für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany

^bFakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany eMail: Kamal.Kumar@mpi-dortmund.mpg.de

,

Franziska Heitkamp

^aMax-Planck-Institute für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany

^bFakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany eMail: Kamal.Kumar@mpi-dortmund.mpg.de

,

Jorgelina L. Pergomet

^aMax-Planck-Institute für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany

,

Felix Otte

^bFakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany eMail: Kamal.Kumar@mpi-dortmund.mpg.de

,

Carsten Strohmann

^bFakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Straße 6, 44227 Dortmund, Germany eMail: Kamal.Kumar@mpi-dortmund.mpg.de

,

Kamal Kumar∗

^aMax-Planck-Institute für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227 Dortmund, Germany

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

In memory of Prof. Dr. Rolf Huisgen

Abstract

An enantioselective hetero-Diels–Alder reaction of alkylidene oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spirooxindole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.

Key words

asymmetric synthesis - hetero-Diels–Alder reaction - spirooxindoles - natural products - hedgehog inhibitors

Volltext

Referenzen

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