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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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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 |
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author | Janganati, Venumadhav Penthala, Narsimha Reddy Madadi, Nikhil Reddy Parkin, Sean Crooks, Peter A. |
author_facet | Janganati, Venumadhav Penthala, Narsimha Reddy Madadi, Nikhil Reddy Parkin, Sean Crooks, Peter A. |
author_sort | Janganati, Venumadhav |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-3998419 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-39984192014-04-24 Monosuccinate ester of melampomagnolide B Janganati, Venumadhav Penthala, Narsimha Reddy Madadi, Nikhil Reddy Parkin, Sean Crooks, Peter A. Acta Crystallogr Sect E Struct Rep Online Organic Papers 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. International Union of Crystallography 2014-02-28 /pmc/articles/PMC3998419/ /pubmed/24765054 http://dx.doi.org/10.1107/S1600536814002815 Text en © Janganati et al. 2014 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Janganati, Venumadhav Penthala, Narsimha Reddy Madadi, Nikhil Reddy Parkin, Sean Crooks, Peter A. Monosuccinate ester of melampomagnolide B |
title | Monosuccinate ester of melampomagnolide B |
title_full | Monosuccinate ester of melampomagnolide B |
title_fullStr | Monosuccinate ester of melampomagnolide B |
title_full_unstemmed | Monosuccinate ester of melampomagnolide B |
title_short | Monosuccinate ester of melampomagnolide B |
title_sort | monosuccinate ester of melampomagnolide b |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998419/ https://www.ncbi.nlm.nih.gov/pubmed/24765054 http://dx.doi.org/10.1107/S1600536814002815 |
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