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Type: Artigo
Title: Total Synthesis Of (-)-marinisporolide C
Author: Dias
Luiz C.; de Lucca
Emilio C.
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.
Editor: Amer Chemical Soc
Rights: fechado
Identifier DOI: 10.1021/acs.joc.7b00023
Date Issue: 2017
Appears in Collections:Unicamp - Artigos e Outros Documentos

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