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A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework
Polyene cyclizations are one of the most powerful and fascinating chemical transformations to rapidly generate molecular complexity. However, cyclizations employing heteroatom‐substituted polyenes are rare. Described here is the tetracyclization of a dual nucleophilic aryl enol ether involving an un...
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/PMC7383491/ https://www.ncbi.nlm.nih.gov/pubmed/32167649 http://dx.doi.org/10.1002/anie.202003127 |
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author | Feilner, Julian M. Wurst, Klaus Magauer, Thomas |
author_facet | Feilner, Julian M. Wurst, Klaus Magauer, Thomas |
author_sort | Feilner, Julian M. |
collection | PubMed |
description | Polyene cyclizations are one of the most powerful and fascinating chemical transformations to rapidly generate molecular complexity. However, cyclizations employing heteroatom‐substituted polyenes are rare. Described here is the tetracyclization of a dual nucleophilic aryl enol ether involving an unprecedented transannular endo‐termination step. In this transformation, five stereocenters, two of which are quaternary, four carbon–carbon bonds, and four six‐membered rings are formed from a readily available cyclization precursor. The realization of this cyclization enabled short synthetic access to the tricyclic diterpenoid pimara‐15‐en‐3α‐8α‐diol. |
format | Online Article Text |
id | pubmed-7383491 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-73834912020-07-27 A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework Feilner, Julian M. Wurst, Klaus Magauer, Thomas Angew Chem Int Ed Engl Communications Polyene cyclizations are one of the most powerful and fascinating chemical transformations to rapidly generate molecular complexity. However, cyclizations employing heteroatom‐substituted polyenes are rare. Described here is the tetracyclization of a dual nucleophilic aryl enol ether involving an unprecedented transannular endo‐termination step. In this transformation, five stereocenters, two of which are quaternary, four carbon–carbon bonds, and four six‐membered rings are formed from a readily available cyclization precursor. The realization of this cyclization enabled short synthetic access to the tricyclic diterpenoid pimara‐15‐en‐3α‐8α‐diol. John Wiley and Sons Inc. 2020-04-01 2020-07-20 /pmc/articles/PMC7383491/ /pubmed/32167649 http://dx.doi.org/10.1002/anie.202003127 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 Feilner, Julian M. Wurst, Klaus Magauer, Thomas A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework |
title | A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework |
title_full | A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework |
title_fullStr | A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework |
title_full_unstemmed | A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework |
title_short | A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework |
title_sort | transannular polyene tetracyclization for rapid construction of the pimarane framework |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7383491/ https://www.ncbi.nlm.nih.gov/pubmed/32167649 http://dx.doi.org/10.1002/anie.202003127 |
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