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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
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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
Consultations : 10/336
Indice de consultation : 2%
Indice de popularité : 0.5%
Résumé     
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  
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