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Absolute configuration of vouacapen-5α-ol
The title compound, C(20)H(30)O(2), {systematic name: (4aR,6aS,7R,11aS,11bR)-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-4a-ol}, is a cassane furanoditerpene which was isolated from the roots of Caesalpinia pulcherrima. The absolute configurations at p...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007238/ https://www.ncbi.nlm.nih.gov/pubmed/21588448 http://dx.doi.org/10.1107/S1600536810029557 |
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author | Fun, Hoong-Kun Yodsaoue, Orapun Chantrapromma, Suchada Karalai, Chatchanok |
author_facet | Fun, Hoong-Kun Yodsaoue, Orapun Chantrapromma, Suchada Karalai, Chatchanok |
author_sort | Fun, Hoong-Kun |
collection | PubMed |
description | The title compound, C(20)H(30)O(2), {systematic name: (4aR,6aS,7R,11aS,11bR)-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-4a-ol}, is a cassane furanoditerpene which was isolated from the roots of Caesalpinia pulcherrima. The absolute configurations at positions 4a, 6a, 7, 11a and 11b are R, S, R, S and R, respectively. The molecule has four-fused rings consisting of three cyclohexane rings and one furan ring. The three cyclohexane rings are trans-fused. Two cyclohexane rings are in chair conformations, while the third is in an envelope conformation. In the crystal structure, the molecules are linked by intermolecular O—H⋯O hydrogen bonds into a zigzag chain along the a axis. A short O⋯O contact [3.0398 (14) Å] is also present. |
format | Text |
id | pubmed-3007238 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30072382010-12-30 Absolute configuration of vouacapen-5α-ol Fun, Hoong-Kun Yodsaoue, Orapun Chantrapromma, Suchada Karalai, Chatchanok Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(20)H(30)O(2), {systematic name: (4aR,6aS,7R,11aS,11bR)-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-4a-ol}, is a cassane furanoditerpene which was isolated from the roots of Caesalpinia pulcherrima. The absolute configurations at positions 4a, 6a, 7, 11a and 11b are R, S, R, S and R, respectively. The molecule has four-fused rings consisting of three cyclohexane rings and one furan ring. The three cyclohexane rings are trans-fused. Two cyclohexane rings are in chair conformations, while the third is in an envelope conformation. In the crystal structure, the molecules are linked by intermolecular O—H⋯O hydrogen bonds into a zigzag chain along the a axis. A short O⋯O contact [3.0398 (14) Å] is also present. International Union of Crystallography 2010-07-31 /pmc/articles/PMC3007238/ /pubmed/21588448 http://dx.doi.org/10.1107/S1600536810029557 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 Chantrapromma, Suchada Karalai, Chatchanok Absolute configuration of vouacapen-5α-ol |
title | Absolute configuration of vouacapen-5α-ol |
title_full | Absolute configuration of vouacapen-5α-ol |
title_fullStr | Absolute configuration of vouacapen-5α-ol |
title_full_unstemmed | Absolute configuration of vouacapen-5α-ol |
title_short | Absolute configuration of vouacapen-5α-ol |
title_sort | absolute configuration of vouacapen-5α-ol |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3007238/ https://www.ncbi.nlm.nih.gov/pubmed/21588448 http://dx.doi.org/10.1107/S1600536810029557 |
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