Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators-Reference-Cited by-同舟云学术

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

Published:2020-08-10 Issue:21 Volume:52 Page:3140-3152
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Kumar Kamal¹,Rehan Mohammad¹,Flegel Jana¹²,Heitkamp Franziska¹²,Pergomet Jorgelina L.¹,Otte Felix²,Strohmann Carsten²

Affiliation:

1. Max-Planck-Institute für Molekulare Physiologie, Abteilung Chemische Biologie

2. Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund

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.

Funder

Max Planck Gesellschaft

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1707222.pdf

Reference10 articles.

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3. Enantio- and diastereoselective hetero-Diels–Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates

4. A Tunable and Enantioselective Hetero-Diels-Alder Reaction Provides Access to Distinct Piperidinoyl Spirooxindoles

5. Unconventional exo selectivity in thermal normal-electron-demand Diels–Alder reactions

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