Cargando…

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...

Descripción completa

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
_version_ 1782313357272940544
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
work_keys_str_mv AT janganativenumadhav monosuccinateesterofmelampomagnolideb
AT penthalanarsimhareddy monosuccinateesterofmelampomagnolideb
AT madadinikhilreddy monosuccinateesterofmelampomagnolideb
AT parkinsean monosuccinateesterofmelampomagnolideb
AT crookspetera monosuccinateesterofmelampomagnolideb