Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/326145
Type: Artigo
Title: Total Synthesis Of (-)-marinisporolide C
Total synthesis of (−)-marinisporolide C
Author: Dias, Luiz C.
Lucca, Jr., Emilio C. de
Abstract: The first total synthesis of (-)-marinisporolide C is described, which establishes unequivocally the relative and absolute configuration of this oxopolyene macrolide. Key features of this synthesis include a series of highly stereoselective aldol reactions followed by directed reductions to build the polyol domain, a Stile cross-coupling reaction to assemble the polyene, and an infra molecular Horner-Wadsworth-Emmons olefination to forge the macrocyclic ring. Despite the initial approach to marinisporolide A using a Yamaguchi macrolactonization reaction that was unsuccessful due to steric hindrance of the oxygen at the C33 position, we were able to prepare a known derivative of marinisporolide A and consequently confirm its stereochemical assignment.
The first total synthesis of (−)-marinisporolide C is described, which establishes unequivocally the relative and absolute configuration of this oxopolyene macrolide. Key features of this synthesis include a series of highly stereoselective aldol reaction
Subject: Síntese total
Reação aldólica
Country: Estados Unidos
Editor: American Chemical Society
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 82, p. 3019 - 3045, 2017.
Rights: Fechado
Identifier DOI: 10.1021/acs.joc.7b00023
Address: https://pubs.acs.org/doi/10.1021/acs.joc.7b00023
Date Issue: 2017
Appears in Collections:IQ - Artigos e Outros Documentos

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