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(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate
The hemisynthesis of the title compound, C(22)H(32)O(2), was carried out through direct acetylation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol]. The molecule is built up from three fus...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998421/ https://www.ncbi.nlm.nih.gov/pubmed/24765017 http://dx.doi.org/10.1107/S1600536814002748 |
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author | Oubabi, Radouane Auhmani, Aziz Ait Itto, My Youssef Auhmani, Abdelwahed Daran, Jean-Claude |
author_facet | Oubabi, Radouane Auhmani, Aziz Ait Itto, My Youssef Auhmani, Abdelwahed Daran, Jean-Claude |
author_sort | Oubabi, Radouane |
collection | PubMed |
description | The hemisynthesis of the title compound, C(22)H(32)O(2), was carried out through direct acetylation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol]. The molecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [−0.10 (6)] allowed this absolute configuration to be confirmed. |
format | Online Article Text |
id | pubmed-3998421 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-39984212014-04-24 (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate Oubabi, Radouane Auhmani, Aziz Ait Itto, My Youssef Auhmani, Abdelwahed Daran, Jean-Claude Acta Crystallogr Sect E Struct Rep Online Organic Papers The hemisynthesis of the title compound, C(22)H(32)O(2), was carried out through direct acetylation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol]. The molecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [−0.10 (6)] allowed this absolute configuration to be confirmed. International Union of Crystallography 2014-02-19 /pmc/articles/PMC3998421/ /pubmed/24765017 http://dx.doi.org/10.1107/S1600536814002748 Text en © Oubabi et al. 2014 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 Oubabi, Radouane Auhmani, Aziz Ait Itto, My Youssef Auhmani, Abdelwahed Daran, Jean-Claude (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate |
title | (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate |
title_full | (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate |
title_fullStr | (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate |
title_full_unstemmed | (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate |
title_short | (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate |
title_sort | (4bs,8as)-1-isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998421/ https://www.ncbi.nlm.nih.gov/pubmed/24765017 http://dx.doi.org/10.1107/S1600536814002748 |
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