A convenient method for the preparation of hydroxyl lactams via regioselective reduction of N-alkyl-3-sulfonyl glutarimides is described. The useful building block is applied to synthesize polysubstituted pyridin-2-one, tacamonine and deplancheine.

1. The key glutarimides were obtained via facile [3+3] annulation. The method featured regioselective introduction of C-6 substituents in glutarimides, and application to the synthesis of natural products and pharmaceuticals. 2. The synthesis of a novel substituted aza-ticyclic compounds through the use of the intramolecular Diels-Alder reaction is present. Further aromaticzation in the present of BF3 to afford 2,3-dihydro-isoindolone.The use of method for the rapid preparation of a substituted isoindolone framework is described.

1. A new route towards the synthesis of drugs and alkaloids by using N-alkylsulfonylacetamide and unsaturated ester as starting materials via stepwise [3+3] annulation. 2. The application of regioselective nucleophilic addition of glutarimide which prepared via stepwise [3+3] annulation. 3. Synthesis of (E)-3-Substituted-N-Alkylacryl-amides and 3,4-Disubstituted Succinimides by using N-alkylsulfonyl-acetamide and alkyl halides as starting materials in the different reaction condition.

Carbon skeleton of polysubstituted pyroglutamates with three contiguous asymmetric centers was built up in one base-induced coupling/cyclization reaction of £\-sulfonylacetamide with 2-bromo-2-propenoates and has been used as the key step in the formal synthesis of isoguvacine paroxetine, and psudoheliotridane.

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Texte remanié de: Thèse de doctorat--Droit--Aix-Marseille 3, 2005. / Bibliogr.p. [491]-532.

No description available.

The indole alkaloids, a class of natural products, have received much synthetic attention for years due to their diverse structures and interesting biological properties. We are particularly interested in synthesizing some of the yohimbine alkaloids extracted from the bark of a tall evergreen African tree (Corynanthe yohimbe, commonly known as fringe tree). Yohimbine and its stereoisomers have been tempting targets for synthetic organic chemists for more than fifty years. These compounds feature a pentacyclic ring system with two heteroatoms and five stereogenic centers. Broadly, the fifteen different synthetic approaches that led to the successful completion of yohimbine alkaloids relied only on two basic synthetic strategies. In the first strategy, the last step almost always was the formation of the C(2)-C(3) bond by either Pictet-Spengler reaction or by Bischler-Napieralski reaction with the concomitant formation of the C ring. The second strategy involved the annulation of the D and E rings onto the intact ABC ring system. With our double annulation methodology, herein, we report a completely different synthetic approach to access the yohimbine alkaloids, and our disconnections are not even remotely close to the synthetic designs used in the past. Our key steps include double Michael reaction to construct the E ring, an intramolecular cyclization to construct the D ring, and finally, the functionality on the D ring can be elaborated to form the C ring of the yohimbine alkaloids.

Despite progress in the metal-catalyzed synthesis of aromatic heterocycles, annulation routes towards 6-membered heterocycles remain underdeveloped. Specifically, routes towards pyridines are rare in spite of the prevalence of this moiety in novel drug candidates. Our initial efforts towards pyridines featured oximes as competent nucleophiles in the intramolecular, 6-exo dig annulation of alkynes using Brønsted acid catalysis. Two of the oxidation states required for subsequent aromatization are contained within the oxime via loss of water. An extension of this chemistry is presented and discussed, and involves the intramolecular metal-catalyzed 6-endo dig annulation of analagous alkynyl-oximes. Additionally, the discovery of a 5-exo dig annulation of related systems is discussed.

Despite progress in the metal-catalyzed synthesis of aromatic heterocycles, annulation routes towards 6-membered heterocycles remain underdeveloped. Specifically, routes towards pyridines are rare in spite of the prevalence of this moiety in novel drug candidates. Our initial efforts towards pyridines featured oximes as competent nucleophiles in the intramolecular, 6-exo dig annulation of alkynes using Brønsted acid catalysis. Two of the oxidation states required for subsequent aromatization are contained within the oxime via loss of water. An extension of this chemistry is presented and discussed, and involves the intramolecular metal-catalyzed 6-endo dig annulation of analagous alkynyl-oximes. Additionally, the discovery of a 5-exo dig annulation of related systems is discussed.