Synthesis of the 4-azatricyclo[5.2.2.0(4,8)]undecan-10-one core of daphniphyllum alkaloid calyciphylline A using a Pd-catalyzed enolate alkenylation |
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Authors: | Solé Daniel Urbaneja Xavier Bonjoch Josep |
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Institution: | Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain. |
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Abstract: | reaction: see text] The ABC ring system of the natural product calyciphylline A has been synthesized. The key steps were a palladium-catalyzed intramolecular coupling of an amino-tethered vinyl bromide with a ketone using potassium phenoxide as the base to generate the C-ring and a hydroxyl-directed hydrogenation of an exocyclic double bond to give the azatricyclic ketone 1. |
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