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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...

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Detalles Bibliográficos
Autores principales: Varga, Szilárd, Angyal, Péter, Martin, Gábor, Egyed, Orsolya, Holczbauer, Tamás, Soós, Tibor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
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.
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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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