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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...

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Detalles Bibliográficos
Autores principales: Oubabi, Radouane, Auhmani, Aziz, Ait Itto, My Youssef, Auhmani, Abdelwahed, Daran, Jean-Claude
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
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.
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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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