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Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions
We report 8‐step syntheses of (−)‐minovincine and (−)‐aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta‐ and hexacyclic frameworks. These cascade transform...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497198/ https://www.ncbi.nlm.nih.gov/pubmed/32351014 http://dx.doi.org/10.1002/anie.202004769 |
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author | Varga, Szilárd Angyal, Péter Martin, Gábor Egyed, Orsolya Holczbauer, Tamás Soós, Tibor |
author_facet | Varga, Szilárd Angyal, Péter Martin, Gábor Egyed, Orsolya Holczbauer, Tamás Soós, Tibor |
author_sort | Varga, Szilárd |
collection | PubMed |
description | We report 8‐step syntheses of (−)‐minovincine and (−)‐aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta‐ and hexacyclic frameworks. These cascade transformations included organocatalytic Michael‐aldol condensation, a multistep anionic Michael‐S(N)2 cascade reaction, and Mannich reaction interrupted Fischer indolization. To streamline the synthetic routes, we also investigated the deliberate use of steric effect to secure various chemo‐ and regioselective transformations. |
format | Online Article Text |
id | pubmed-7497198 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-74971982020-09-25 Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions Varga, Szilárd Angyal, Péter Martin, Gábor Egyed, Orsolya Holczbauer, Tamás Soós, Tibor Angew Chem Int Ed Engl Communications We report 8‐step syntheses of (−)‐minovincine and (−)‐aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta‐ and hexacyclic frameworks. These cascade transformations included organocatalytic Michael‐aldol condensation, a multistep anionic Michael‐S(N)2 cascade reaction, and Mannich reaction interrupted Fischer indolization. To streamline the synthetic routes, we also investigated the deliberate use of steric effect to secure various chemo‐ and regioselective transformations. John Wiley and Sons Inc. 2020-06-03 2020-08-03 /pmc/articles/PMC7497198/ /pubmed/32351014 http://dx.doi.org/10.1002/anie.202004769 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/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Varga, Szilárd Angyal, Péter Martin, Gábor Egyed, Orsolya Holczbauer, Tamás Soós, Tibor Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions |
title | Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions |
title_full | Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions |
title_fullStr | Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions |
title_full_unstemmed | Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions |
title_short | Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions |
title_sort | total syntheses of (−)‐minovincine and (−)‐aspidofractinine through a sequence of cascade reactions |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497198/ https://www.ncbi.nlm.nih.gov/pubmed/32351014 http://dx.doi.org/10.1002/anie.202004769 |
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