Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades

[Image: see text] Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation...

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Autores principales: Jones, Benjamin T., García-Cárceles, Javier, Caiger, Lewis, Hazelden, Ian R., Lewis, Richard J., Langer, Thomas, Bower, John F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8485351/
https://www.ncbi.nlm.nih.gov/pubmed/34546043
http://dx.doi.org/10.1021/jacs.1c08615
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author Jones, Benjamin T.
García-Cárceles, Javier
Caiger, Lewis
Hazelden, Ian R.
Lewis, Richard J.
Langer, Thomas
Bower, John F.
author_facet Jones, Benjamin T.
García-Cárceles, Javier
Caiger, Lewis
Hazelden, Ian R.
Lewis, Richard J.
Langer, Thomas
Bower, John F.
author_sort Jones, Benjamin T.
collection PubMed
description [Image: see text] Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C–H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
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spelling pubmed-84853512021-10-01 Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades Jones, Benjamin T. García-Cárceles, Javier Caiger, Lewis Hazelden, Ian R. Lewis, Richard J. Langer, Thomas Bower, John F. J Am Chem Soc [Image: see text] Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C–H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry. American Chemical Society 2021-09-21 2021-09-29 /pmc/articles/PMC8485351/ /pubmed/34546043 http://dx.doi.org/10.1021/jacs.1c08615 Text en © 2021 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 Jones, Benjamin T.
García-Cárceles, Javier
Caiger, Lewis
Hazelden, Ian R.
Lewis, Richard J.
Langer, Thomas
Bower, John F.
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades
title Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades
title_full Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades
title_fullStr Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades
title_full_unstemmed Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades
title_short Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C–H Functionalization Cascades
title_sort complex polyheterocycles and the stereochemical reassignment of pileamartine a via aza-heck triggered aryl c–h functionalization cascades
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8485351/
https://www.ncbi.nlm.nih.gov/pubmed/34546043
http://dx.doi.org/10.1021/jacs.1c08615
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