Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step

The gold(I)‐catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)‐1,4‐disubstituted 1,3‐butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user‐friendly procedure. Reaction of acetylene with 1,5‐dien...

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Autores principales: Scharnagel, Dagmar, Escofet, Imma, Armengol‐Relats, Helena, de Orbe, M. Elena, Korber, J. Nepomuk, Echavarren, Antonio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7078946/
https://www.ncbi.nlm.nih.gov/pubmed/31912609
http://dx.doi.org/10.1002/anie.201915895
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author Scharnagel, Dagmar
Escofet, Imma
Armengol‐Relats, Helena
de Orbe, M. Elena
Korber, J. Nepomuk
Echavarren, Antonio M.
author_facet Scharnagel, Dagmar
Escofet, Imma
Armengol‐Relats, Helena
de Orbe, M. Elena
Korber, J. Nepomuk
Echavarren, Antonio M.
author_sort Scharnagel, Dagmar
collection PubMed
description The gold(I)‐catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)‐1,4‐disubstituted 1,3‐butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user‐friendly procedure. Reaction of acetylene with 1,5‐dienes gives rise stereoselectively to tricyclo[5.1.0.0(2,4)]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.
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spelling pubmed-70789462020-03-19 Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step Scharnagel, Dagmar Escofet, Imma Armengol‐Relats, Helena de Orbe, M. Elena Korber, J. Nepomuk Echavarren, Antonio M. Angew Chem Int Ed Engl Communications The gold(I)‐catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)‐1,4‐disubstituted 1,3‐butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user‐friendly procedure. Reaction of acetylene with 1,5‐dienes gives rise stereoselectively to tricyclo[5.1.0.0(2,4)]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone. John Wiley and Sons Inc. 2020-01-31 2020-03-16 /pmc/articles/PMC7078946/ /pubmed/31912609 http://dx.doi.org/10.1002/anie.201915895 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ 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
Scharnagel, Dagmar
Escofet, Imma
Armengol‐Relats, Helena
de Orbe, M. Elena
Korber, J. Nepomuk
Echavarren, Antonio M.
Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
title Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
title_full Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
title_fullStr Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
title_full_unstemmed Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
title_short Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
title_sort acetylene as a dicarbene equivalent for gold(i) catalysis: total synthesis of waitziacuminone in one step
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7078946/
https://www.ncbi.nlm.nih.gov/pubmed/31912609
http://dx.doi.org/10.1002/anie.201915895
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