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The synthesis of two diastereomeric seco-rhazinilams with opposite atropomeric chiralities |
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| Authors: | Jean Lévy Mustapha Soufyane Catherine Mirand Michèle Döéde Maindreville Daniel Royer |
| Institution: | a Laboratoire de Transformations et Synthèse de Substances Naturelles, associé au CNRS, Université de Reims Champagne-Ardenne, Faculté de Pharmacie, 51, rue Cognacq-Jay, F-51096, Reims, France b Département de Chimie, Faculté des Sciences, 24000, El Jadida, Maroc |
| Abstract: | (−)-Tabersonine 4 was submitted to quaternization and Emde degradation to yield the 3,4-seco derivative 5, which was hydrolyzed and decarboxylated to the diastereomeric indolenines 8 and 9. Oxidative rearrangement of 8 and 9 yielded the two diastereomeric seco-rhazinilams (−)-10 and (+)-11, differing in the atropomeric conformations of their biarylic system. The results are discussed in the realm of oxidation and rearrangements in the aspidosperma series of indole alkaloids. |
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