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Synthesis and biological evaluation of sugars containing α,β-Unsaturated γ-Lactones
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Orientador(es)
Resumo(s)
The stereocontrolled synthesis of new sugar derivatives carrying the α,β-unsaturated δ-lactone (butenolide) moiety is described. Sugar-fused or sugar-linked butenolides can be constructed by an efficient reaction sequence involving Wittig olefination of 3- or 5-keto sugars and intramolecular cyclization of the intermediate γ-hydroxy α,β-unsaturated esters. The antimicrobial activities of the products and that of a known sugar-derived pyranoid α,β-unsaturated δ-lactone were investigated against six pathogenic bacteria and six fungi. The pyranoid α,β-unsaturated δ-lactone 29 proved to be the most active compound in this series towards the plant pathogenic fungi Colletotrichum coffeanum (coffee berry disease) and Pyricularia oryzae (rice blast disease).
Descrição
Palavras-chave
Witting reaction lactones Carbohydrates Lactona Hidrato de carbono
Contexto Educativo
Citação
Xavier, N. M; Silva, S.; Madeira, P. J. A; Florêncio, M. H.; Silva, F. V. M.1 ; Justino, J.1; Thiem, J.; Rauter, A. P. (2008) - Synthesis and biological evaluation of sugars containing α,β-Unsaturated γ-Lactones.European journal of organic chemistry, 36: 6134-6143.DOI: 10.1002/ejoc.200800763