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Monaco A, Aliev AE, Hilton ST. Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives. Chemistry. 2015;21(40):13909-12doi: 10.1002/chem.201502436.
Monaco, A., Aliev, A. E., & Hilton, S. T. (2015). Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives. Chemistry (Weinheim an der Bergstrasse, Germany), 21(40), 13909-12. https://doi.org/10.1002/chem.201502436
Monaco, Alessandra, et al. "Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,40 (2015): 13909-12. doi: https://doi.org/10.1002/chem.201502436
Monaco A, Aliev AE, Hilton ST. Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives. Chemistry. 2015 Sep 28;21(40):13909-12. doi: 10.1002/chem.201502436. PMID: 26376327.
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Chemistry. 2015 Sep 28;21(40):13909-12. doi: 10.1002/chem.201502436.

Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives.

Chemistry (Weinheim an der Bergstrasse, Germany)

Alessandra Monaco, Abil E Aliev, Stephen T Hilton

Affiliations

  1. UCL School of Pharmacy, University College London, 29-39?Brunswick Square, London, WC1N 1AX (UK).
  2. Department of Chemistry, University College London, 20?Gordon Street, London, WC1H 0AJ (UK).
  3. UCL School of Pharmacy, University College London, 29-39?Brunswick Square, London, WC1N 1AX (UK). [email protected].

PMID: 26376327 DOI: 10.1002/chem.201502436

Abstract

Compounds that comprise the erythrina alkaloid class of natural products are based on a tetracyclic spiroamine framework and exhibit a range of biological activities on the central nervous system. Herein, we report a new and efficient total synthesis of this multiple-ring system based on an intramolecular acylal cyclisation (IAC) approach. Using this methodology, the tetracyclic core was rapidly assembled over a two-step domino process catalysed by a Lewis acid. The effect of heteroatoms, substituents and ring size on the IAC has also been investigated, and the broad application of this procedure is demonstrated by the synthesis of a library of derivatives in good yields with excellent regioselectivity.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Lewis acid; acylal; erythrina alkaloids; intramolecular acylal cyclisation; tandem cyclisation

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