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Archambaud, S., Legrand, F., Aphecetche-Julienne, K., Collet, S., Guingant, A. & Evain, M. (2010) Total Synthesis of (+)-Brefeldin C, (+)-nor-Me Brefeldin A and (+)-4-epi-nor-Me Brefeldin A. Eur. J. Org. Chem. 1364–1380.
Added by: Laurent Cournède (2016-03-10 21:37:33) |
| Type de référence: Article DOI: 10.1002/ejoc.200901233 Numéro d'identification (ISBN etc.): 1434-193X Clé BibTeX: Archambaud2010 Voir tous les détails bibliographiques  |
Catégories: MIOPS Mots-clés: Asymmetric synthesis, asymmetric-synthesis, Brefeldin A analogues, carboxylic-acids, cinchona alkaloids, cyclic anhydrides, Desymmetrization, direct addition, enantioselective synthesis, formal synthesis, G protein, guanine-nucleotide, Macrocycles, Macrolactonization, macrolide antibiotics, nucleotide-exchange factor, Total synthesis Créateurs: Aphecetche-Julienne, Archambaud, Collet, Evain, Guingant, Legrand Collection: Eur. J. Org. Chem. |
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| Résumé |
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A total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed, Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the absolute configuration at C4 of BFC, a Suzuki-Miyaura cross-coupling reaction to create the C11-C12 bond and a Yamaguchi reaction to form the 13-membered lactone ring.
Added by: Laurent Cournède |