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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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Autores principales: Fun, Hoong-Kun, Yodsaoue, Orapun, Chantrapromma, Suchada, Karalai, Chatchanok
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
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.
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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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