New Insights into Cyclobutenone Rearrangements: A Total Synthesis of the Natural ROS-Generating Anti-Cancer Agent Cribrostatin (ROS=reactive-oxygen species)
Mubina Mohamed1, Théo P. Gonçalves1, Richard J. Whitby1, Helen F. Sneddon2, David C. Harrowven1
- 1Dept of Chemistry, University of Southampton, UK
- 2GSK Medicines Research Centre, Stevenage, UKRead the publication that featured this abstract
Aryl- and heteroarylcyclobutenone rearrangements proceed in excellent yield under continuous-flow conditions. The former shows a Hammett correlation with σI providing strong evidence that electrocyclisation is the rate-determining step and has a late transition state. The reaction has been modelled by using DFT and CCSD(T) methods, with the latter giving excellent correlation with the experimental rate constant. A short and efficient total synthesis of cribrostatin 6, an anti-neoplastic and anti-microbial agent, provides a topical demonstration of the value of this method.
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