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Synthesis 2019; 51(07): 1491-1515
DOI: 10.1055/s-0037-1611715
DOI: 10.1055/s-0037-1611715
review
Deployment of Aziridines for the Synthesis of Alkaloids and Their Derivatives
This work was supported by the National Research Foundation of Korea (NRF-2012M3A7B4049645 and 2014R1A5A1011165 with Centre for New Directions in Organic Synthesis).Further Information
Publication History
Received: 06 November 2018
Accepted after revision: 17 December 2018
Publication Date:
18 February 2019 (online)
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
-
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For selected reviews of piperidine alkaloids, see:
Representative references, for isolation, see:
For activity, see: