Method of synthesizing camptothecin-relating compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S394000

Reexamination Certificate

active

07378555

ABSTRACT:
The present invention is to prepare efficiently 2′-amino-5′-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.

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Josien et al., “A General Synthetic Approach to the (20S)-Camptothecin Family of Antitumor Agents by a Regiocontrolled cascade Radical Cyclization of Aryl Isonitriles,” Chemistry a European Journal, 1998, vol. 4, No. 1, pp. 67-83.
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She et al., “Concise Total Syntheses of dl-Camptothecin and Related Anticancer Drugs,” J. Org. Chem. 1993, 58, 611-617.
Henegar et al., “Practical Asymmetric Synthesis of (S)-4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyranol[3,4-f]indolizine-3,6,10(4H)-trione, a Key Intermediate for the Synthesis of Irinotecan and Other Camptothecin analogs,” J. Org. Chem., 1997, vol. 62, No. 19, pp. 6588-6597.
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