Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

Abstract

Various (activated and non-activated) aziridines with diverse substitution patterns have been deployed successfully as starting materials for the synthesis of a wide variety of alkaloids via suitable functionalization and aziridine ring transformation. Alternatively, the preparation and interception of reactive aziridine intermediates has also been shown to constitute a valid approach toward alkaloid synthesis. This review summarizes aziridine-mediated syntheses of alkaloids, in which the aziridine is mobilized as either a substrate or an advanced synthetic intermediate.

1 Introduction

2 Alkaloids Synthesis from Aziridine Starting Materials

2.1 (2R)- and (2S)-Hydroxymethyl-N-(1-phenylethyl)aziridines

2.2 N-Benzylaziridine-2-carboxylates

2.3 2-Substituted N-Tosyl- or N-Tritylaziridines

2.4 2,3-Disubstituted N-Cbz- or N-Tosylaziridines

2.5 N-DMB-aziridines

3 Alkaloids Synthesis from Aziridines as Key Advanced Synthetic Intermediates

3.1 Alkylative Aziridine Ring Opening

3.2 Arylative Aziridine Ring Opening

3.3 Ring Expansion

3.4 Oxidative Aziridine Ring Opening

3.5 Heteroatomic Nucleophilic Aziridine Ring Opening

3.6 Reductive Aziridine Ring Opening

4 Conclusion

Key words

aziridine - ring strain - iminosugars - alkaloids - natural products

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