Barnes, NG;
Ahmed Mal Ullah, AA;
Ragazzon, PA;
Charafi, N;
Hadfield, JA;
(2021)
Syntheses of Combretastatin A‐4 and Related Stilbenes by Using Aqueous Conditions.
ChemistrySelect
, 6
(28)
pp. 7082-7086.
10.1002/slct.202101960.
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Abstract
Combretastatin A-4 (CA4) is a potent anti-mitotic and vascular disrupting agent. Organic chemists have been working to optimize the synthesis of CA4 for the past 3 decades, with methods requiring hazardous solvents and harsh reaction conditions. Here, we report the synthesis of CA4 and a variety of stilbenes in an aqueous Wittig system. Potassium carbonate or lithium hydroxide were used as base in this Wittig reaction to give excellent yields of mixtures of E- and Z-stilbenes. The synthesis of CA4 was achieved using tetrahydropyran (THP) or silyl protected phenolic aldehydes. The THP groups were removed using dilute acid whilst the silyl groups fortuitously fell off during work up.
| Type: | Article |
|---|---|
| Title: | Syntheses of Combretastatin A‐4 and Related Stilbenes by Using Aqueous Conditions |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/slct.202101960 |
| Publisher version: | http://dx.doi.org/10.1002/slct.202101960 |
| Language: | English |
| Additional information: | © 2021 The Authors. ChemistrySelect published by Wiley-VCH GmbH This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
| Keywords: | Combretastatins, Green Chemistry, Stilbenes, Water Chemistry, Wittig Chemistry |
| UCL classification: | UCL 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/10132003 |
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