Bioorganic & Medicinal Chemistry Letters 2003-02-10

Selective phenolic acylation of 10-hydroxycamptothecin using poly (ethylene glycol) carboxylic acid.

Richard B Greenwald, Yun H Choe, Dechun Wu

Index: Bioorg. Med. Chem. Lett. 13(3) , 577-80, (2003)

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Abstract

Selective acylation of the phenolic hydroxyl group of 10-hydroxycamptothecin has been accomplished using phenyl dichlorophosphate. Additional modification of the 10-OH as an ether permits a 20-acyl derivative to be synthesized. This result along with data from a 6-hydroxyquinoline model strongly suggests that powerful intermolecular hydrogen bonding exists in the parent molecule.