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6α-Acetoxy­gedunin

The title compound [systematic name: (1S,3aS,4aR,4bS,5S,6R,6aR,10aR,10bR,12aS)-5,6-bis­(acet­yloxy)-1-(3-fur­yl)-1,5,6,6a,7,10a,10b,11,12,12a-deca­hydro-4b,7,7,10a,12a-penta­methyl­oxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione], C(30)H(36)O(9), is a limonoid-type triterpene isolated from Aglai...

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Detalles Bibliográficos
Autores principales: Hofer, Margit, Greger, Harald, Mereiter, Kurt
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977213/
https://www.ncbi.nlm.nih.gov/pubmed/21583624
http://dx.doi.org/10.1107/S1600536809027998
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author Hofer, Margit
Greger, Harald
Mereiter, Kurt
author_facet Hofer, Margit
Greger, Harald
Mereiter, Kurt
author_sort Hofer, Margit
collection PubMed
description The title compound [systematic name: (1S,3aS,4aR,4bS,5S,6R,6aR,10aR,10bR,12aS)-5,6-bis­(acet­yloxy)-1-(3-fur­yl)-1,5,6,6a,7,10a,10b,11,12,12a-deca­hydro-4b,7,7,10a,12a-penta­methyl­oxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione], C(30)H(36)O(9), is a limonoid-type triterpene isolated from Aglaia elaeagnoidea (A. Juss.) Benth. (Meliaceae) from Queensland, northern Australia. It contains the gedunin core of four trans-fused six-membered rings with an oxirane ring annelated to the fourth ring. A terminal 3-furyl unity and two acet­oxy groups in a mutual cis-disposition supplement the mol­ecule. A comparison between the gedunin cores of the title compound, the parent compound gedunin, and three further gedunin derivatives revealed considerable variations in their conformation stemming from the conformational lability of the first screw-boat ring and the third twist-boat ring. A sensitive measure for the third ring is one C—C—C—C torsion angle, which is 14.2 (2)° in the title compound, but varies in other cases from ca 20 to ca −40°. In the crystalline state, 6α-acetoxy­gedunin shows ten comparatively weak C—H⋯O inter­actions, with H⋯O distances in the range of 2.33–2.69 Å.
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spelling pubmed-29772132010-12-30 6α-Acetoxy­gedunin Hofer, Margit Greger, Harald Mereiter, Kurt Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound [systematic name: (1S,3aS,4aR,4bS,5S,6R,6aR,10aR,10bR,12aS)-5,6-bis­(acet­yloxy)-1-(3-fur­yl)-1,5,6,6a,7,10a,10b,11,12,12a-deca­hydro-4b,7,7,10a,12a-penta­methyl­oxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione], C(30)H(36)O(9), is a limonoid-type triterpene isolated from Aglaia elaeagnoidea (A. Juss.) Benth. (Meliaceae) from Queensland, northern Australia. It contains the gedunin core of four trans-fused six-membered rings with an oxirane ring annelated to the fourth ring. A terminal 3-furyl unity and two acet­oxy groups in a mutual cis-disposition supplement the mol­ecule. A comparison between the gedunin cores of the title compound, the parent compound gedunin, and three further gedunin derivatives revealed considerable variations in their conformation stemming from the conformational lability of the first screw-boat ring and the third twist-boat ring. A sensitive measure for the third ring is one C—C—C—C torsion angle, which is 14.2 (2)° in the title compound, but varies in other cases from ca 20 to ca −40°. In the crystalline state, 6α-acetoxy­gedunin shows ten comparatively weak C—H⋯O inter­actions, with H⋯O distances in the range of 2.33–2.69 Å. International Union of Crystallography 2009-07-22 /pmc/articles/PMC2977213/ /pubmed/21583624 http://dx.doi.org/10.1107/S1600536809027998 Text en © Hofer et al. 2009 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
Hofer, Margit
Greger, Harald
Mereiter, Kurt
6α-Acetoxy­gedunin
title 6α-Acetoxy­gedunin
title_full 6α-Acetoxy­gedunin
title_fullStr 6α-Acetoxy­gedunin
title_full_unstemmed 6α-Acetoxy­gedunin
title_short 6α-Acetoxy­gedunin
title_sort 6α-acetoxy­gedunin
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977213/
https://www.ncbi.nlm.nih.gov/pubmed/21583624
http://dx.doi.org/10.1107/S1600536809027998
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