Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes

[Image: see text] We present the first total synthesis of eight ent-pimaranes via a short and enantioselective route (11–16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Brønsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydr...

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Autores principales: Plangger, Immanuel, Wurst, Klaus, Magauer, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7613685/
https://www.ncbi.nlm.nih.gov/pubmed/36170466
http://dx.doi.org/10.1021/acs.orglett.2c02843
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author Plangger, Immanuel
Wurst, Klaus
Magauer, Thomas
author_facet Plangger, Immanuel
Wurst, Klaus
Magauer, Thomas
author_sort Plangger, Immanuel
collection PubMed
description [Image: see text] We present the first total synthesis of eight ent-pimaranes via a short and enantioselective route (11–16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Brønsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydrogenation for rapid access to a late synthetic branching point. From there on, selective functional group manipulations enable the synthesis of ent-pimaranes bearing different modifications in the A- and C-rings.
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spelling pubmed-76136852022-10-08 Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes Plangger, Immanuel Wurst, Klaus Magauer, Thomas Org Lett [Image: see text] We present the first total synthesis of eight ent-pimaranes via a short and enantioselective route (11–16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Brønsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydrogenation for rapid access to a late synthetic branching point. From there on, selective functional group manipulations enable the synthesis of ent-pimaranes bearing different modifications in the A- and C-rings. American Chemical Society 2022-09-28 2022-10-07 /pmc/articles/PMC7613685/ /pubmed/36170466 http://dx.doi.org/10.1021/acs.orglett.2c02843 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Plangger, Immanuel
Wurst, Klaus
Magauer, Thomas
Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes
title Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes
title_full Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes
title_fullStr Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes
title_full_unstemmed Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes
title_short Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes
title_sort short, divergent, and enantioselective total synthesis of bioactive ent-pimaranes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7613685/
https://www.ncbi.nlm.nih.gov/pubmed/36170466
http://dx.doi.org/10.1021/acs.orglett.2c02843
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AT magauerthomas shortdivergentandenantioselectivetotalsynthesisofbioactiveentpimaranes

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