Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/86686
Type: Artigo de periódico
Title: Coibacins A And B: Total Synthesis And Stereochemical Revision
Author: Carneiro V.M.T.
Avila C.M.
Balunas M.J.
Gerwick W.H.
Pilli R.A.
Abstract: The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent antiinflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A. © 2013 American Chemical Society.
Editor: American Chemical Society
Rights: fechado
Identifier DOI: 10.1021/jo402339y
Address: http://www.scopus.com/inward/record.url?eid=2-s2.0-84896768719&partnerID=40&md5=f18ed384f5a512f45760e6975dc995d9
Date Issue: 2014
Appears in Collections:Unicamp - Artigos e Outros Documentos

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