Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols**

Three natural aromadendrane sesquiterpenes, (−)-epiglobulol, (−)-4β,7α-aromadendranediol, and (−)-4α,7α-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17 % overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which for...

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Autores principales: Carreras, Javier, Livendahl, Madeleine, McGonigal, Paul R, Echavarren, Antonio M
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4298797/
https://www.ncbi.nlm.nih.gov/pubmed/24692360
http://dx.doi.org/10.1002/anie.201402044
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author Carreras, Javier
Livendahl, Madeleine
McGonigal, Paul R
Echavarren, Antonio M
author_facet Carreras, Javier
Livendahl, Madeleine
McGonigal, Paul R
Echavarren, Antonio M
author_sort Carreras, Javier
collection PubMed
description Three natural aromadendrane sesquiterpenes, (−)-epiglobulol, (−)-4β,7α-aromadendranediol, and (−)-4α,7α-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17 % overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds.
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spelling pubmed-42987972015-01-27 Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols** Carreras, Javier Livendahl, Madeleine McGonigal, Paul R Echavarren, Antonio M Angew Chem Int Ed Engl Communications Three natural aromadendrane sesquiterpenes, (−)-epiglobulol, (−)-4β,7α-aromadendranediol, and (−)-4α,7α-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17 % overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds. WILEY-VCH Verlag 2014-05-05 2014-04-01 /pmc/articles/PMC4298797/ /pubmed/24692360 http://dx.doi.org/10.1002/anie.201402044 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. https://creativecommons.org/licenses/by-nc/4.0/ © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Carreras, Javier
Livendahl, Madeleine
McGonigal, Paul R
Echavarren, Antonio M
Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols**
title Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols**
title_full Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols**
title_fullStr Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols**
title_full_unstemmed Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols**
title_short Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (−)-Epiglobulol and (−)-4β,7α- and (−)-4α,7α-Aromadendranediols**
title_sort gold(i) as an artificial cyclase: short stereodivergent syntheses of (−)-epiglobulol and (−)-4β,7α- and (−)-4α,7α-aromadendranediols**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4298797/
https://www.ncbi.nlm.nih.gov/pubmed/24692360
http://dx.doi.org/10.1002/anie.201402044
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