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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Oxidative and reductive transformations of epothilone A.

The C7 hydroxy group of cytotoxic epothilone A was selectively oxidized using PDC. A selective oxidation of the C3 hydroxy group was accomplished with Me2S/(PhCO2)2 after in situ protection of C7-OH. Reduction of epothilone A or of a C5, C7 dioxo derivative with NaBH4 proceeded at the C5 carbonyl group. Oxidation and hydrogenation of the C16-C17 double bond proved to be difficult but it was easily cleaved with ozone and the resulting keto derivative was transformed to epothilone analogs with different side chains.[1]

References

  1. Oxidative and reductive transformations of epothilone A. Sefkow, M., Kiffe, M., Schummer, D., Höfle, G. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
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