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

Jones, Benjamin T, Garcia-Carceles, Javier, Caiger, Lewis, Hazelden, Ian R, Lewis, Richard J, Langer, Thomas and Bower, John F ORCID: 0000-0002-7551-8221 (2021) Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 143 (38). pp. 15593-15598.

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Official URL: http://dx.doi.org/10.1021/jacs.1c08615

Abstract

Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses <i>N</i>-(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.

Item Type:	Article
Divisions:	Faculty of Science and Engineering > School of Physical Sciences
Depositing User:	Symplectic Admin
Date Deposited:	04 Oct 2021 16:02
Last Modified:	18 Jan 2023 21:27
DOI:	10.1021/jacs.1c08615
Open Access URL:	https://doi.org/10.1021/jacs.1c08615
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3139279