Monaco, A;
Aliev, AE;
Hilton, ST;
(2015)
Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives.
Chemistry - A European Journal
, 21
(40)
pp. 13909-13912.
10.1002/chem.201502436.
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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.
| Type: | Article |
|---|---|
| Title: | Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/chem.201502436 |
| Publisher version: | http://dx.doi.org/10.1002/chem.201502436 |
| Language: | English |
| Additional information: | This is the peer reviewed version of the following article: Monaco, A; Aliev, AE; Hilton, ST; (2015) Intramolecular Acylal Cyclisation (IAC) as an Efficient Synthetic Strategy towards the Total Synthesis of Erythrina Alkaloid Derivatives. Chemistry - A European Journal , 21 (40) pp. 13909-13912, which has been published in final form at http://dx.doi.org/10.1002/chem.201502436. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/1471012 |
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