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Syntheses of Combretastatin A-4 and Related Stilbenes by Using Aqueous Conditions

Barnes, Natalie G.; Ahmed Mal Ullah, Amjed A.; Ragazzon, Patricia A.; Charafi, Nadia; Hadfield, John A.

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Authors

Natalie G. Barnes

Amjed A. Ahmed Mal Ullah

Nadia Charafi

John A. Hadfield



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.

Journal Article Type Article
Acceptance Date Jul 19, 2021
Online Publication Date Jul 26, 2021
Publication Date Jul 27, 2021
Publicly Available Date May 30, 2023
Journal ChemistrySelect
Print ISSN 2365-6549
Publisher Wiley
Volume 6
Issue 28
Pages 7082 - 7086
DOI https://doi.org/10.1002/slct.202101960
Keywords General Chemistry
Publisher URL https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202101960

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