Chiron Approach to Formal Synthesis of 8,9-dideoxyneodysiherbaine (MSVIII-19)

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AudienciaPúblico en generales_ES
CoberturaMéxicoes_ES
Fecha de ingreso2026-10-05T16:32:33Z
Fecha de publicación2017-01-01
ResumenBackground: The synthesis of biologically active model compounds represents a valuable tool for medicinal chemistry. In this regard, the synthesis of MSVII-19, a structurally simplified model compound of Dysiherbaine, developed by the group of Sasaki, was synthesized with the intention of preparing a powerful agonist or antagonist of glutamate receptor. Therefore, the synthesis of an advanced intermediate in the Sasaki's synthesis of MSVIII-19 is reported. Methods: Taking advantage of the furanose ring of the diacetone-D-glucose (DAG), the cis-fused hexahydrofuro{[}3,2-b] pyran ring system of the title compound was constructed by featuring two protocols: SHOWO (sequential hydrolysis-oxidation-Wittig olefination) and RCM (ring closing metathesis). Then, by applying a combined allylation at the anomeric position and a Pd-catalyzed double bond isomerization reaction, the methyl ester group in 1b was installed. Results: The synthesis of an advanced intermediate of MSVIII-19 involves three key procedures: a) SHOWO (sequential hydrolysis-oxidation-Wittig olefination) protocol; b) RCM (ring closing metathesis) reaction; y c) the nucleophilic substitution at the anomeric position. Additionally, with the use of a cheaper starting material (DAG) than that used in the previous synthesis (tri-O-acetyl-D-glucal). The current synthesis is truly competitive with that reported by the Sasaki group. Conclusion: A concise formal total synthesis of the advanced intermediate of MSVIII-19 was achieved. (Current synthesis: 14 steps; previous synthesis 20 steps).es_ES
Doihttps://doi.org/10.2174/1570178614666170307091943es_ES
URIhttps://riuat.uat.edu.mx/handle/123456789/4378
Idiomaenes_ES
EditorialBENTHAM SCIENCE PUBL LTDes_ES
RelaciónLetters in Organic Chemistryes_ES
URL relacionadohttps://doi.org/10.2174/1570178614666170307091943es_ES
DerechosAcceso restringido / Suscripción (Metadatos de producción científica)es_ES
Licenciahttp://purl.org/coar/access_right/c_16eces_ES
FuenteLetters in Organic Chemistry
Palabra claveChiron approaches_ES
Palabra clavedysiherbaine (DH)es_ES
Palabra claveformal synthesises_ES
Palabra clavehexahydrofuro{[}3,2-b]pyranes_ES
Palabra claveMSVII-19es_ES
Palabra claveneodysiherbaine (NDH)es_ES
Palabra clavering closing metathesises_ES
Palabra claveSHOWOes_ES
TítuloChiron Approach to Formal Synthesis of 8,9-dideoxyneodysiherbaine (MSVIII-19)es_ES
TipoArtículoes_ES
ArbitradoHa sido Arbitradoes_ES
AutorSanchez-Eleuterio, Alma
AutorMastranzo, Virginia M.
AutorQuintero, Leticia
AutorSartillo-Piscil, Fernando
AutorSanchez-Eleuterio, Almaes_ES
AutorMastranzo, Virginia M.es_ES
AutorQuintero, Leticiaes_ES
AutorSartillo-Piscil, Fernandoes_ES
InstituciónUniversidad Autónoma de Tamaulipas
InstituciónUniversidad Autónoma de Tamaulipases_ES
Número4es_ES
Rango de páginas261-266es_ES
URL relacionadahttps://doi.org/10.2174/1570178614666170307091943
Tipo de artículoIndexado
Tipo de artículoIndexadoes_ES
Volumen14es_ES

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