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Absolute configuration of isoeichlerialactone

The title seco-dammarane triterpenoid, C(27)H(42)O(4) (systematic name: 3-{(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(R)-2-methyl-5-oxotetra­hydro­furan-2-yl]-7-(prop-1-en-2-yl)dodeca­hydro-1H-cyclo­penta­[a]naphthalen-6-yl}propanoic acid), has been isolated for the first time from the seeds o...

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Autores principales: Fun, Hoong-Kun, Joycharat, Nantiya, Voravuthikunchai, Supayang Piyawan, Chantrapromma, Suchada
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2984085/
https://www.ncbi.nlm.nih.gov/pubmed/21580698
http://dx.doi.org/10.1107/S1600536810009499
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author Fun, Hoong-Kun
Joycharat, Nantiya
Voravuthikunchai, Supayang Piyawan
Chantrapromma, Suchada
author_facet Fun, Hoong-Kun
Joycharat, Nantiya
Voravuthikunchai, Supayang Piyawan
Chantrapromma, Suchada
author_sort Fun, Hoong-Kun
collection PubMed
description The title seco-dammarane triterpenoid, C(27)H(42)O(4) (systematic name: 3-{(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(R)-2-methyl-5-oxotetra­hydro­furan-2-yl]-7-(prop-1-en-2-yl)dodeca­hydro-1H-cyclo­penta­[a]naphthalen-6-yl}propanoic acid), has been isolated for the first time from the seeds of Aglaia forbesii. The mol­ecule has three fused rings and all rings are in trans-fused. The two cyclo­hexane rings are in standard chair conformations and the cyclo­pentane ring adopts an envelope conformation. Its absolute configuration was determined by the refinement of the Flack parameter to 0.26 (17). In the crystal, mol­ecules are linked into chains along [010] by O—H⋯O hydrogen bonds.
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spelling pubmed-29840852010-12-30 Absolute configuration of isoeichlerialactone Fun, Hoong-Kun Joycharat, Nantiya Voravuthikunchai, Supayang Piyawan Chantrapromma, Suchada Acta Crystallogr Sect E Struct Rep Online Organic Papers The title seco-dammarane triterpenoid, C(27)H(42)O(4) (systematic name: 3-{(3S,3aR,5aR,6S,7S,9aR,9bR)-6,9a,9b-trimethyl-3-[(R)-2-methyl-5-oxotetra­hydro­furan-2-yl]-7-(prop-1-en-2-yl)dodeca­hydro-1H-cyclo­penta­[a]naphthalen-6-yl}propanoic acid), has been isolated for the first time from the seeds of Aglaia forbesii. The mol­ecule has three fused rings and all rings are in trans-fused. The two cyclo­hexane rings are in standard chair conformations and the cyclo­pentane ring adopts an envelope conformation. Its absolute configuration was determined by the refinement of the Flack parameter to 0.26 (17). In the crystal, mol­ecules are linked into chains along [010] by O—H⋯O hydrogen bonds. International Union of Crystallography 2010-03-20 /pmc/articles/PMC2984085/ /pubmed/21580698 http://dx.doi.org/10.1107/S1600536810009499 Text en © Fun et al. 2010 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
Fun, Hoong-Kun
Joycharat, Nantiya
Voravuthikunchai, Supayang Piyawan
Chantrapromma, Suchada
Absolute configuration of isoeichlerialactone
title Absolute configuration of isoeichlerialactone
title_full Absolute configuration of isoeichlerialactone
title_fullStr Absolute configuration of isoeichlerialactone
title_full_unstemmed Absolute configuration of isoeichlerialactone
title_short Absolute configuration of isoeichlerialactone
title_sort absolute configuration of isoeichlerialactone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2984085/
https://www.ncbi.nlm.nih.gov/pubmed/21580698
http://dx.doi.org/10.1107/S1600536810009499
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