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|All Authors / Contributors:||
Florence Bonnaterre; Jieping Zhu; Université de Paris-Sud. Faculté des Sciences d'Orsay (Essonne).
|Description:||1 vol. (280 p.) ; 30 cm.|
|Responsibility:||Florence Bonnaterre ; sous la direction de [Jieping Zhu].|
The project was divided in several parts. First we have focused on the total synthesis of an alcaloid, (-)-norsuaveoline. In a few steps, we have been able to synthesize one of the key-intermadiates of the synthesis, an oxazole prepared from natural (-)-tryptophane. In a second part we have developped rapid diversity-oriented access to highly-functionalized heterocycles, via Ugi reaction / intramolecular cyclizations (amidations or direct arylations) sequences. We have developped two complementary and chemoselective sequences for the synthesis of oxindoles and dihydrophenenthridines, from readily available reagents. These syntheses are of great synthetic efficiency, and enable easy 4-points variations on the molecule. In a last part, we have carried out preliminary studies to synthesize physostigmine with an original approach, based on tandem radicalar reaction: cyclization / trapping of the radical / beta-scission. The first results were promising and demonstrated that this reaction can afford the key-intermediate in the synthesis of physostigmine.