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Synthetic Approaches Towards Alkaloids Bearing α-tertiary Amines.

A. Hager, N. Vrielink, D. Hager, J. Lefranc, D. Trauner
Published 2016 · Chemistry, Medicine

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Alkaloids account for some of the most beautiful and biologically active natural products. Although they are usually classified along biosynthetic criteria, they can also be categorized according to certain structural motifs. Amongst these, the α-tertiary amine (ATA), i.e. a tetrasubstituted carbon atom surrounded by three carbons and one nitrogen, is particularly interesting. A limited number of methods have been described to access this functional group and fewer still are commonly used in synthesis. Herein, we review some approaches to asymmetrically access ATAs and provide an overview of alkaloid total syntheses where those have been employed.
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The α-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of β-methylene C–H bonds† †Electronic supplementary information (ESI) available: Experimental procedures, characterization data and kinetic details. CCDC 1570476. For ESI and crystallographic data in CIF or other
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Nitrogen-bridged, natural product-like octahydrobenzofurans and octahydroindoles: scope and mechanism of bridge-forming reductive amination via caged heteroadamantanes
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Tandem Oxidative Derivatization of Nitrene Insertion Products for the Highly Diastereoselective Synthesis of 1,3-aminoalcohols.
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Regio- and chemoselective synthesis of nitrogen-containing heterocycles via the oxidative cascade cyclization of unactivated 1,n-enynes.
Mohana Reddy Mutra (2020)
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