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Synthesis of position-specific tritium-labeled 20(S)-camptothecin, 9-amino-20(S)-camptothecin, and 10,11-methylenedioxy-20(S)-camptothecin

✍ Scribed by Allan W. Nicholas; Mansukh C. Wani; Monroe E. Wall; John A. Kepler; George F. Taylor

Publisher: John Wiley and Sons
Year: 1993
Tongue: French
Weight: 474 KB
Volume: 33
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580330907

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The synthesis is given for three ring A tritiated camptothecin (CPT) analogs as biological probes in the study of the parent compounds which are of current widespread interest as potent anticancer agents. The strategy of catalytic tritolysis of aryl halide bonds was employed, and thus the preparations of the requisite precursors 9‐chloro‐20(S)‐CPT (9), 9‐amino‐10,12‐dibromo‐20(S)‐CPT (14), and 9‐chloro‐10,11‐methylenedioxy‐20(S)‐CPT (18) are given; catalytic tritiation of these respective precursors under polar, alkaline solvent conditions using palladium/carbon provides smooth conversion to [9‐^3^H]‐20(S)‐CPT (10), 9‐amino‐[10,12‐^3^H]‐20(S)‐CPT (15), and [9‐^3^H]‐10,11‐methylenedioxy‐20(S)‐CPT (19).

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