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Legrand, F., Archambaud, S., Collet, S., Aphecetche-Julienne, K., Guingant, A. & Evain, M. (2008) Enantioselective synthesis of an advanced intermediate for the synthesis of brefeldin A and analogues. Synlett, 389–393.
Added by: Laurent Cournède (2016-03-10 21:58:42) |
| Type de référence: Article DOI: 10.1055/s-2008-1032041 Numéro d'identification (ISBN etc.): 0936-5214 Clé BibTeX: Legrand2008 Voir tous les détails bibliographiques  |
Catégories: MIOPS Mots-clés: activation, anhydrides, arf, brefeldin A, cinchona alkaloids, desymmetrization reaction, gtp-binding proteins, inhibition, mechanism, nucleotide-exchange factor, sec7, specificity, Takai reaction Créateurs: Aphecetche-Julienne, Archambaud, Collet, Evain, Guingant, Legrand Collection: Synlett |
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| Résumé |
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A synthesis of methyl (1R,2R,4S)-2-[(E)-2-iodovinyl]-4-(methoxymethoxy)cyclopentanecarboxylate is described in nine steps from a prochiral anhydride. A desymmetrization reaction followed by an epimerization and a Takai reaction are the key steps of the transformation. Based on previous work, this vinylic iodide product should be a useful precursor for the synthesis of brefeldin A and analogues.
Added by: Laurent Cournède |