Beilstein J. Org. Chem.2008,4, No. 15, doi:10.3762/bjoc.4.15
indanetrione 8, but attempts with bromoindanone 18 resulted in no reaction even under reflux. Utilization of a milder oxidant phenyliodosyl bis(trifluoroacetate) (PIFA) [33] for the oxidation of phenolic indanone 20, derived from 18 by selective demethylation with magnesium iodide (MgI2) [34], gave
Beilstein J. Org. Chem.2006,2, No. 13, doi:10.1186/1860-5397-2-13
, is essential for microtubule binding activity, as change of the keto group to a thioketo group or demethylation of the OMe group in this ring reduced the activity [31](reviewed in [2]). Demethylation of the OMe group in ring A also decreased the activity, indicating the importance of this ring for
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Graphical Abstract
Scheme 1:
Reagents and conditions for synthesis of N-glutaryl-deacetylcolchicine. The reagents used at each s...