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Published on: March 6, 2019
The synthesis of melohenine B and a related natural product
Christopher S Lancefield1, Linna Zhou, Tomas Lébl
1School of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews, Fife KY16 9ST, UK.
Abstract:
A concise synthesis of melohenine B and O-ethyl-14-epimelohenine B, from eburnamonine, was achieved via a biomimetic diastereoselective singlet oxygen-mediated oxidative cleavage of the indole C2-C7 bond. These studies enabled the assignment of the absolute configuration of the natural products. In line with a proposed biosynthetic pathway, the resulting nine-membered ring containing products could be converted to the corresponding quinolones.
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