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Total Synthesis of the Diterpene Waihoensene

A racemic and scalable enantioselective total synthesis of (+)‐waihoensene was accomplished. (+)‐Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all‐cis‐fused, containing six contiguous stereo...

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Autores principales: Rosenbaum, Lisa‐Catherine, Häfner, Maximilian, Gaich, Tanja
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/PMC7898921/
https://www.ncbi.nlm.nih.gov/pubmed/33103334
http://dx.doi.org/10.1002/anie.202011298
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author Rosenbaum, Lisa‐Catherine
Häfner, Maximilian
Gaich, Tanja
author_facet Rosenbaum, Lisa‐Catherine
Häfner, Maximilian
Gaich, Tanja
author_sort Rosenbaum, Lisa‐Catherine
collection PubMed
description A racemic and scalable enantioselective total synthesis of (+)‐waihoensene was accomplished. (+)‐Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all‐cis‐fused, containing six contiguous stereocenters, four of which are quaternary. These structural features were efficiently installed by means of a diastereoselective radical cyclization, followed by an intramolecular Pauson–Khand reaction, a diastereoselective α‐alkylation, and a diastereoselective 1,4‐addition reaction. Enantioselectivity was introduced at an early stage, by an asymmetric palladium catalyzed decarboxylative allylation reaction on gram scale.
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spelling pubmed-78989212021-03-03 Total Synthesis of the Diterpene Waihoensene Rosenbaum, Lisa‐Catherine Häfner, Maximilian Gaich, Tanja Angew Chem Int Ed Engl Communications A racemic and scalable enantioselective total synthesis of (+)‐waihoensene was accomplished. (+)‐Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all‐cis‐fused, containing six contiguous stereocenters, four of which are quaternary. These structural features were efficiently installed by means of a diastereoselective radical cyclization, followed by an intramolecular Pauson–Khand reaction, a diastereoselective α‐alkylation, and a diastereoselective 1,4‐addition reaction. Enantioselectivity was introduced at an early stage, by an asymmetric palladium catalyzed decarboxylative allylation reaction on gram scale. John Wiley and Sons Inc. 2020-12-10 2021-02-08 /pmc/articles/PMC7898921/ /pubmed/33103334 http://dx.doi.org/10.1002/anie.202011298 Text en © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the http://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
Rosenbaum, Lisa‐Catherine
Häfner, Maximilian
Gaich, Tanja
Total Synthesis of the Diterpene Waihoensene
title Total Synthesis of the Diterpene Waihoensene
title_full Total Synthesis of the Diterpene Waihoensene
title_fullStr Total Synthesis of the Diterpene Waihoensene
title_full_unstemmed Total Synthesis of the Diterpene Waihoensene
title_short Total Synthesis of the Diterpene Waihoensene
title_sort total synthesis of the diterpene waihoensene
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898921/
https://www.ncbi.nlm.nih.gov/pubmed/33103334
http://dx.doi.org/10.1002/anie.202011298
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