Abstract
Artemisinin, a sesquiterpene which contains a labile endo-peroxide, is a promising new antimalarial drug. In order to prepare new derivatives that retain the peroxide group critical for biological activity, we employed several derivatives of dihydroartemisinin as substrates for the fungus Beauveria sulfurescens. The best substrate, arteether, yielded two mono-hydroxylated products. In the major product the C-14 methyl had been oxidized whereas the minor product contained a 9β-hydroxyl group. The structures and stereochemistry of the biotransformation products were established by mass spectrometry, 1- and 2D-NMR. The compounds were used as intermediates in the preparation of labelled compounds, an isomeric alcohol and other derivatives. This was the first time the endoperoxide group had not been destroyed in the course of introducing hydroxyl groups in an artemisinin derivative.
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Ziffer, H., Hu, Y., Pu, Y. (1992). Beauveria Sulfurescens Mediated Oxidation of Dihydroartemisinin Derivatives. In: Servi, S. (eds) Microbial Reagents in Organic Synthesis. NATO ASI Series, vol 381. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-2444-7_29
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DOI: https://doi.org/10.1007/978-94-011-2444-7_29
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