Rapid and diverse route to natural product-like biaryl ether containing macrocycles |
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Authors: | Pierre CristauJean-Pierre Vors Jieping Zhu |
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Institution: | a Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, cedex 91198, France b Bayer CropScience, 14-20 Rue Pierre Baizet, Lyon 69009, France |
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Abstract: | A two-step sequence involving an Ugi four-component reaction and an intramolecular nucleophilic aromatic substitution (SNAr) has been developed for the rapid access to biaryl-ether containing macrocycles. In the course of this study, we documented that ammonium chloride can promote the Ugi-4CR in non-polar aprotic solvent (toluene) without the interference of an alternative Passerini reaction. Solid phase synthesis of macrocycles by this two-step sequence was also developed using polymer (Wang resin) supported α-(4′-fluoro-3′-nitro)phenethyl isocyanoacetate as one of the inputs. |
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Keywords: | multicomponent reaction Ugi-4CR intramolecular SNAr reaction cycloetherification marcrocycles diaryl ether |
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