Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition

A 14‐step synthesis of (+)‐cochlearol B is reported. This renoprotective meroterpenoid features a unique core structure containing a densely substituted cyclobutane ring with three stereocenters. Our strategy employed an organocatalytic Kabbe condensation in route to the key chromenyl triflate. A su...

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Autores principales: Richardson, Alistair D., Vogel, Trenton R., Traficante, Emily F., Glover, Kason J., Schindler, Corinna S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401860/
https://www.ncbi.nlm.nih.gov/pubmed/35417620
http://dx.doi.org/10.1002/anie.202201213
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author Richardson, Alistair D.
Vogel, Trenton R.
Traficante, Emily F.
Glover, Kason J.
Schindler, Corinna S.
author_facet Richardson, Alistair D.
Vogel, Trenton R.
Traficante, Emily F.
Glover, Kason J.
Schindler, Corinna S.
author_sort Richardson, Alistair D.
collection PubMed
description A 14‐step synthesis of (+)‐cochlearol B is reported. This renoprotective meroterpenoid features a unique core structure containing a densely substituted cyclobutane ring with three stereocenters. Our strategy employed an organocatalytic Kabbe condensation in route to the key chromenyl triflate. A subsequent Catellani reaction incorporated the remaining carbon atoms featured in the skeleton of cochlearol B. An ensuing visible‐light‐mediated [2+2] photocycloaddition closed the cyclobutane and formed the central bicyclo[3.2.0]heptane core. Notably, careful design and tuning of the Catellani and photocycloaddition reactions proved crucial in overcoming undesired reactivity, including cyclopropanation reactions and [4+2] cycloadditions.
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spelling pubmed-94018602022-08-26 Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition Richardson, Alistair D. Vogel, Trenton R. Traficante, Emily F. Glover, Kason J. Schindler, Corinna S. Angew Chem Int Ed Engl Communications A 14‐step synthesis of (+)‐cochlearol B is reported. This renoprotective meroterpenoid features a unique core structure containing a densely substituted cyclobutane ring with three stereocenters. Our strategy employed an organocatalytic Kabbe condensation in route to the key chromenyl triflate. A subsequent Catellani reaction incorporated the remaining carbon atoms featured in the skeleton of cochlearol B. An ensuing visible‐light‐mediated [2+2] photocycloaddition closed the cyclobutane and formed the central bicyclo[3.2.0]heptane core. Notably, careful design and tuning of the Catellani and photocycloaddition reactions proved crucial in overcoming undesired reactivity, including cyclopropanation reactions and [4+2] cycloadditions. John Wiley and Sons Inc. 2022-06-23 2022-08-01 /pmc/articles/PMC9401860/ /pubmed/35417620 http://dx.doi.org/10.1002/anie.202201213 Text en © 2022 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 Communications
Richardson, Alistair D.
Vogel, Trenton R.
Traficante, Emily F.
Glover, Kason J.
Schindler, Corinna S.
Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition
title Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition
title_full Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition
title_fullStr Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition
title_full_unstemmed Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition
title_short Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition
title_sort total synthesis of (+)‐cochlearol b by an approach based on a catellani reaction and visible‐light‐enabled [2+2] cycloaddition
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401860/
https://www.ncbi.nlm.nih.gov/pubmed/35417620
http://dx.doi.org/10.1002/anie.202201213
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