ANTITUMOR AGENTS .75. SYNTHESIS OF CYTOTOXIC ANTHRAQUINONES DIGIFERRUGINOL AND MORINDAPARVIN-B
ANTITUMOR AGENTS .75. SYNTHESIS OF CYTOTOXIC ANTHRAQUINONES DIGIFERRUGINOL AND MORINDAPARVIN-B
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DOI：
10.1021/np50042a011
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发表时间：
1985-11-01
影响因子：
5.1
通讯作者：
LEE, KH
中科院分区：
文献类型：
--
作者：
CHANG, P;LEE, KH
描述了二甲红醇 (4) 和巴戟天-B (10) 的简单有效的合成。 1-羟基蒽醌的 Marschalk 反应得到 1-羟基-2-甲基蒽醌 (2)。用 N-溴代琥珀酰亚胺和过氧化苯甲酰处理 2，得到 1-羟基-2-溴甲基蒽醌 (3)，用 AgNO3 将其定量转化为 4。 1,5-二羟基蒽醌的甲基化产生二甲醚(6)，其用三氟化硼部分去甲基化为二氟硼螯合物(7)。用碱性 HCHO 和连二硫酸钠处理 7，得到 1-羟基-2-羟甲基-5-甲氧基蒽醌 (9)。 9的5-甲基醚与生成的三溴化物裂解得到10。
A simple and efficient synthesis of digiferruginol (4) and morindaparvin-B (10) is described. Marschalk reaction of 1-hydroxyanthraquinone afforded 1-hydroxy-2-methylanthraquinone (2). Treatment of 2 with N-bromosuccinimide and benzoyl peroxide led to 1-hydroxy-2-bromomethylanthraquinone (3), which was converted to 4 with AgNO3 in quantitative yield. Methylation of 1,5-dihydroxyanthraquinone yielded a diemthyl ether (6), which was partially demethylated with boron trifluoride to a difluoroboron chelate (7). Treatment of 7 with alkaline HCHO and sodium dithionate gave rise to 1-hydroxy-2-hydroxymethyl-5-methoxyanthraquinone (9). Cleavage of the 5-methyl ether of 9 with born tribromide furnished 10.