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Redetermination and absolute configuration of 7α-hy­droxy­royleanone

The title compound [systematic name: 7α,12-dihy­droxy-8,12-abietadiene,11,14-dione or (4bS,8aS,10R)-3,10-dihy­droxy-2-isopropyl-4b,8,8-trimethyl-1,4,4b,5,6,7,8,8a,9,10-deca­hydro­phenanthrene-1,4-dione], C(20)H(28)O(4), is an abietane diterpen­oid, which was isolated from the roots of Premna obtusif...

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Autores principales: Razak, Ibrahim Abdul, Salae, Abdul Wahab, Chantrapromma, Suchada, Karalai, Chatchanok, Fun, Hoong-Kun
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3006754/
https://www.ncbi.nlm.nih.gov/pubmed/21587809
http://dx.doi.org/10.1107/S1600536810020544
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author Razak, Ibrahim Abdul
Salae, Abdul Wahab
Chantrapromma, Suchada
Karalai, Chatchanok
Fun, Hoong-Kun
author_facet Razak, Ibrahim Abdul
Salae, Abdul Wahab
Chantrapromma, Suchada
Karalai, Chatchanok
Fun, Hoong-Kun
author_sort Razak, Ibrahim Abdul
collection PubMed
description The title compound [systematic name: 7α,12-dihy­droxy-8,12-abietadiene,11,14-dione or (4bS,8aS,10R)-3,10-dihy­droxy-2-isopropyl-4b,8,8-trimethyl-1,4,4b,5,6,7,8,8a,9,10-deca­hydro­phenanthrene-1,4-dione], C(20)H(28)O(4), is an abietane diterpen­oid, which was isolated from the roots of Premna obtusifolia (Verbenaceae). Its crystal structure has been reported previously [Chen et al. (2000 ▶). Jiegou Huaxue, 19, 122–125], but the absolute configuration could not be determined using data collected with Mo radiation. This redetermination using Cu radiation shows the the absolute configurations of the stereogenic centres at positions 4b, 8a and 10 to be S, S and R, respectively. Two intra­molecular O—H⋯O hydrogen bonds [one generating an S(5) ring and one generating an S(6) ring] and a number of short C—H⋯O contacts occur. In the crystal, mol­ecules are linked into infinite chains propagating in [100] by O—H⋯O hydrogen bonds and weak C—H⋯O inter­actions.
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spelling pubmed-30067542010-12-30 Redetermination and absolute configuration of 7α-hy­droxy­royleanone Razak, Ibrahim Abdul Salae, Abdul Wahab Chantrapromma, Suchada Karalai, Chatchanok Fun, Hoong-Kun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound [systematic name: 7α,12-dihy­droxy-8,12-abietadiene,11,14-dione or (4bS,8aS,10R)-3,10-dihy­droxy-2-isopropyl-4b,8,8-trimethyl-1,4,4b,5,6,7,8,8a,9,10-deca­hydro­phenanthrene-1,4-dione], C(20)H(28)O(4), is an abietane diterpen­oid, which was isolated from the roots of Premna obtusifolia (Verbenaceae). Its crystal structure has been reported previously [Chen et al. (2000 ▶). Jiegou Huaxue, 19, 122–125], but the absolute configuration could not be determined using data collected with Mo radiation. This redetermination using Cu radiation shows the the absolute configurations of the stereogenic centres at positions 4b, 8a and 10 to be S, S and R, respectively. Two intra­molecular O—H⋯O hydrogen bonds [one generating an S(5) ring and one generating an S(6) ring] and a number of short C—H⋯O contacts occur. In the crystal, mol­ecules are linked into infinite chains propagating in [100] by O—H⋯O hydrogen bonds and weak C—H⋯O inter­actions. International Union of Crystallography 2010-06-05 /pmc/articles/PMC3006754/ /pubmed/21587809 http://dx.doi.org/10.1107/S1600536810020544 Text en © Razak 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
Razak, Ibrahim Abdul
Salae, Abdul Wahab
Chantrapromma, Suchada
Karalai, Chatchanok
Fun, Hoong-Kun
Redetermination and absolute configuration of 7α-hy­droxy­royleanone
title Redetermination and absolute configuration of 7α-hy­droxy­royleanone
title_full Redetermination and absolute configuration of 7α-hy­droxy­royleanone
title_fullStr Redetermination and absolute configuration of 7α-hy­droxy­royleanone
title_full_unstemmed Redetermination and absolute configuration of 7α-hy­droxy­royleanone
title_short Redetermination and absolute configuration of 7α-hy­droxy­royleanone
title_sort redetermination and absolute configuration of 7α-hy­droxy­royleanone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3006754/
https://www.ncbi.nlm.nih.gov/pubmed/21587809
http://dx.doi.org/10.1107/S1600536810020544
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