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Synthesis of an azabicyclic framework towards (±)-actinophyllic acid |
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| Authors: | Danny Mortimer Matthew Whiting Joseph PA Harrity Simon Jones Iain Coldham |
| Institution: | 1. Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK;2. GlaxoSmithKline Research and Development, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK |
| Abstract: | Lewis acid mediated intramolecular Mannich reaction between an azocinone and a 3-formylindole was investigated as part of a study towards the synthesis of actinophyllic acid. The intramolecular Mannich reaction resulted in a single diastereomer of the 1-azabicyclo4.2.1]nonan-5-one core framework, although single crystal X-ray structure analysis revealed that this had the undesired stereochemistry in comparison with the natural product. |
| Keywords: | Mannich Indole Actinophyllic acid 1-Azabicyclo[4 2 1]nonane Azocinone |
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