2-Substituted-3,7-dinitro-11-oxatricycloundec-9-ene: an approach towards the synthesis of Ergot alkaloids |
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| Authors: | Shatha Younis Mahmood Lina Sader-Bakaouni Philippe Vérité François Tillequin |
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| Institution: | a Laboratoire de Pharmacognosie, UMR 8638, Faculté des Sciences Pharmaceutiques et Biologiques, Université René-Descartes, 4, Avenue de l'Observatoire, 75270 Paris Cedex 06, France
b Laboratoire de Chimie Analytique, UFR de Médecine et Pharmacie, 22 Boulevard Gambetta, 76183 Rouen Cedex 1, France |
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| Abstract: | A simple and versatile method for the preparation of various ergoline or secoergoline skeleton, using 2-substituted-3,7-dinitro-11-oxatricycloundec-9-ene as key intermediates, is described. The key step involves an IMDAF reaction with an excellent stereocontrol. This novel synthetic route provides new cycloadducts as useful scaffolds for Ergot alkaloids synthesis. |
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| Keywords: | Ergot alkaloids Ergoline Secoergoline Lysergic acid IMDAF Oxatricycloundec-9-ene compounds |
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