A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide

Ir‐catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established (13)C‐NMR method to determine the enantioselectivity of each methyl‐branched stere...

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Autores principales: Andringa, Ruben L. H., de Kok, Niels A. W., Driessen, Arnold J. M., Minnaard, Adriaan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362178/
https://www.ncbi.nlm.nih.gov/pubmed/33929790
http://dx.doi.org/10.1002/anie.202104759
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author Andringa, Ruben L. H.
de Kok, Niels A. W.
Driessen, Arnold J. M.
Minnaard, Adriaan J.
author_facet Andringa, Ruben L. H.
de Kok, Niels A. W.
Driessen, Arnold J. M.
Minnaard, Adriaan J.
author_sort Andringa, Ruben L. H.
collection PubMed
description Ir‐catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established (13)C‐NMR method to determine the enantioselectivity of each methyl‐branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.
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spelling pubmed-83621782021-08-17 A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide Andringa, Ruben L. H. de Kok, Niels A. W. Driessen, Arnold J. M. Minnaard, Adriaan J. Angew Chem Int Ed Engl Research Articles Ir‐catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established (13)C‐NMR method to determine the enantioselectivity of each methyl‐branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency. John Wiley and Sons Inc. 2021-06-04 2021-08-02 /pmc/articles/PMC8362178/ /pubmed/33929790 http://dx.doi.org/10.1002/anie.202104759 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Andringa, Ruben L. H.
de Kok, Niels A. W.
Driessen, Arnold J. M.
Minnaard, Adriaan J.
A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide
title A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide
title_full A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide
title_fullStr A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide
title_full_unstemmed A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide
title_short A Unified Approach for the Total Synthesis of cyclo‐Archaeol, iso‐Caldarchaeol, Caldarchaeol, and Mycoketide
title_sort unified approach for the total synthesis of cyclo‐archaeol, iso‐caldarchaeol, caldarchaeol, and mycoketide
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8362178/
https://www.ncbi.nlm.nih.gov/pubmed/33929790
http://dx.doi.org/10.1002/anie.202104759
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