Barnes, NG, Ahmed Mal Ullah, AA, Ragazzon, PA, Charafi, N and Hadfield, JA (2021) Syntheses of Combretastatin A‐4 and Related Stilbenes by Using Aqueous Conditions. ChemistrySelect, 6 (28). 7082 - 7086.

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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.

Item Type: Article
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.
Uncontrolled Keywords: combratastatins; Green Chemistry; Stilbenes; Water Chemistry; Writing Chemistry
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Chemical and Physical Sciences
Depositing User: Symplectic
Date Deposited: 17 Aug 2021 09:49
Last Modified: 17 Nov 2021 15:27
URI: https://eprints.keele.ac.uk/id/eprint/9878

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