Abstract
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.
Highlights
1 Introduction 2 Methods used for the installation of a-tertiary amines 2.1 A C,C-bond is formed in the step that generates the ATA 2.2 A C,N-bond is formed in the step that generates the ATA 3 Homotropane alkaloids 4 Histrionicotoxins 5 Lycopodium alkaloids 6 Hasubanan alkaloids 7 Stemona alkaloids 8 Indole alkaloids 9 Cephalotaxines Erythrina alkaloids Indolizidine and quinolizidine alkaloids Lactacystine and salinosporamide Manzacidins Tetrodotoxin Miscellaneous alkaloids Conclusions Acknowledgements Notes and references antifeedants or as mediators of ecologically bene cial interactions.[1]
We have provided a survey of syntheses that feature the installation of an a-tertiary amine (ATA) as a common thread
This structural motif is widespread amongst alkaloids and has physicochemical consequences, such as increased lipophilicity and chromatographic mobility that distinguishes its bearers from other basic amines
Summary
Review this review and in keeping with the literature, we de ne an ATA as a nitrogen atom bound to a sp3-hybridized carbon that bears three additional carbon–carbon bonds. While our review is by no means comprehensive, we hope to feature the most instructive examples for the Anastasia Hager studied chemistry in Wurzburg, conducting her Diploma thesis on natural product isolation and synthesis with Prof. D. Trauner's research group for an internship at UC Berkeley, she moved to Munich for her PhD work that was centered on the development of biomimetic syntheses of complex natural products implementing cascade reactions. Fiedler at Princeton University developing novel chemical tools to allow for investigations of inositol pyrophosphate signaling pathway She works as a laboratory head in process research at Bayer in Wuppertal. Bringmann, working on the development of an axial-chirality transfer concept For his graduate work he joined the laboratory of Prof. We hope that this review will bene t the design of synthetic pathways toward drugs and synthetic building blocks that contain a-tertiary amines
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