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Scholarly Works, Virginia Tech Center for Drug Discovery

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https://hdl.handle.net/10919/91897

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Browsing Scholarly Works, Virginia Tech Center for Drug Discovery by Subject "514/376"

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    Method for the conversion of cephalomannine to taxol and for the preparation of n-acyl analogs of taxol
    (United States Patent and Trademark Office, 1995-11-28)
    The natural product cephalomannine can be converted to the important anticancer natural product taxol by a simple process involving the steps of dihydroxylation to give cephalomannine-diols, diol cleavage, benzoylation at the 2'-position and reaction with a 1,2-diamine. The same process when applied to mixtures of taxol and cephalomannine makes it possible to separate taxol from cephalomannine-diols by simple flash-chromatography after the dihydroxylation step. If the benzoylation step is avoided in the above sequence of conversions, the process leads to the free amine (N-debenzoyltaxol). In addition, the selection of an acylating reagent other than that with the benzoyl group for acylation of the free amine (N-debenzoyltaxol), allows the preparation of taxol analogs with other N-acyl substituents.