Cargando…

Absolute configuration of isovouacapenol C

The title compound, C(27)H(34)O(5) {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihy­droxy-4,4,7,11b-tetra­methyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodeca­hydro­phenanthro[3,2-b]furan-5-yl benzoate}, is a cassane furan­oditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The...

Descripción completa

Detalles Bibliográficos
Autores principales: Fun, Hoong-Kun, Yodsaoue, Orapun, Karalai, Chatchanok, Chantrapromma, Suchada
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007289/
https://www.ncbi.nlm.nih.gov/pubmed/21588364
http://dx.doi.org/10.1107/S1600536810028023
_version_ 1782194321045323776
author Fun, Hoong-Kun
Yodsaoue, Orapun
Karalai, Chatchanok
Chantrapromma, Suchada
author_facet Fun, Hoong-Kun
Yodsaoue, Orapun
Karalai, Chatchanok
Chantrapromma, Suchada
author_sort Fun, Hoong-Kun
collection PubMed
description The title compound, C(27)H(34)O(5) {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihy­droxy-4,4,7,11b-tetra­methyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodeca­hydro­phenanthro[3,2-b]furan-5-yl benzoate}, is a cassane furan­oditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The three cyclo­hexane rings are trans fused: two of these are in chair conformations with the third in a twisted half-chair conformation, whereas the furan ring is almost planar (r.m.s. deviation = 0.003 Å). An intra­molecular C—H⋯O inter­action generates an S(6) ring. The absolute configurations of the stereogenic centres at positions 4a, 5, 6, 6a, 7, 11a and 11b are R, R, R, S, R, S and R, respectively. In the crystal, mol­ecules are linked into infinite chains along [010] by O—H⋯O hydrogen bonds. C⋯O [3.306 (2)–3.347 (2) Å] short contacts and C—H⋯π inter­actions also occur.
format Text
id pubmed-3007289
institution National Center for Biotechnology Information
language English
publishDate 2010
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-30072892010-12-30 Absolute configuration of isovouacapenol C Fun, Hoong-Kun Yodsaoue, Orapun Karalai, Chatchanok Chantrapromma, Suchada Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(27)H(34)O(5) {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihy­droxy-4,4,7,11b-tetra­methyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodeca­hydro­phenanthro[3,2-b]furan-5-yl benzoate}, is a cassane furan­oditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The three cyclo­hexane rings are trans fused: two of these are in chair conformations with the third in a twisted half-chair conformation, whereas the furan ring is almost planar (r.m.s. deviation = 0.003 Å). An intra­molecular C—H⋯O inter­action generates an S(6) ring. The absolute configurations of the stereogenic centres at positions 4a, 5, 6, 6a, 7, 11a and 11b are R, R, R, S, R, S and R, respectively. In the crystal, mol­ecules are linked into infinite chains along [010] by O—H⋯O hydrogen bonds. C⋯O [3.306 (2)–3.347 (2) Å] short contacts and C—H⋯π inter­actions also occur. International Union of Crystallography 2010-07-17 /pmc/articles/PMC3007289/ /pubmed/21588364 http://dx.doi.org/10.1107/S1600536810028023 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
Yodsaoue, Orapun
Karalai, Chatchanok
Chantrapromma, Suchada
Absolute configuration of isovouacapenol C
title Absolute configuration of isovouacapenol C
title_full Absolute configuration of isovouacapenol C
title_fullStr Absolute configuration of isovouacapenol C
title_full_unstemmed Absolute configuration of isovouacapenol C
title_short Absolute configuration of isovouacapenol C
title_sort absolute configuration of isovouacapenol c
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007289/
https://www.ncbi.nlm.nih.gov/pubmed/21588364
http://dx.doi.org/10.1107/S1600536810028023
work_keys_str_mv AT funhoongkun absoluteconfigurationofisovouacapenolc
AT yodsaoueorapun absoluteconfigurationofisovouacapenolc
AT karalaichatchanok absoluteconfigurationofisovouacapenolc
AT chantraprommasuchada absoluteconfigurationofisovouacapenolc