Synthesis of 1-fluoro-, 4-fluoro-, and 1, 4-difluoro-4-demethoxydaunomycinone. Interesting D-ring analogs of adriamycin

…, JS Swenton, JA Filppi, RL Wolgemuth

文献索引：Morrow; Swenton; Filppi; Wolgemuth Journal of Organic Chemistry, 1987 , vol. 52, # 5 p. 713 - 719

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被引用次数: 28

摘要

The syntheses of racemic 1-fluoro-(4), 4-flUOrO-(5), and 1, 4-difluoro-4- demethoxydaunomycinone (6) as well as the (+) antipodes of the latter two compounds are reported. The synthetic route involved the annelation of a highly functionalized quinone monoketal with the appropriate cyanophthalide anion followed by deprotection. The cyanophthalides were obtained from the corresponding hydroxyphthalides, prepared by ...