Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

Lingamurthy Macha; Matthias D’hooghe; Hyun-Joon Ha

doi:10.1055/s-0037-1611715

Synthesis, Table of Contents

Synthesis 2019; 51(07): 1491-1515
DOI: 10.1055/s-0037-1611715

review

Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives

Lingamurthy Macha

^aDepartment of Chemistry, Hankuk University of Foreign Studies, Yongin 17035, South Korea Email: hjha@hufs.ac.kr

,

Matthias D’hooghe *

^bSynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium Email: Matthias.Dhooghe@UGent.be

,

Hyun-Joon Ha*

^aDepartment of Chemistry, Hankuk University of Foreign Studies, Yongin 17035, South Korea Email: hjha@hufs.ac.kr

› Author Affiliations

Abstract

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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

Full Text

References

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