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Monosuccinate ester of melampomagnolide B

The title monosuccinate derivative of melampomagnolide B [systematic name: 4-(((1aR,7aS,10aS,10bS,E)-1a-methyl-8-meth­yl­ene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-deca­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-5-yl)meth­oxy)-4-oxo­butan­oic acid], C(19)H(24)O(7), was obtained from the reaction of m...

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Detalles Bibliográficos
Autores principales: Janganati, Venumadhav, Penthala, Narsimha Reddy, Madadi, Nikhil Reddy, Parkin, Sean, Crooks, Peter A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998419/
https://www.ncbi.nlm.nih.gov/pubmed/24765054
http://dx.doi.org/10.1107/S1600536814002815
Descripción
Sumario:The title monosuccinate derivative of melampomagnolide B [systematic name: 4-(((1aR,7aS,10aS,10bS,E)-1a-methyl-8-meth­yl­ene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-deca­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-5-yl)meth­oxy)-4-oxo­butan­oic acid], C(19)H(24)O(7), was obtained from the reaction of melampomagnolide B with succinic anhydride under nucleophilic addition reaction conditions. The mol­ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The inter­nal double bond in the ten-membered ring has the cis geometry (i.e. it is the E isomer). The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O—H⋯O hydrogen bonds link the mol­ecules into chains parallel to the b-axis direction.