Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene
Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene
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1,8-二羟基萘双 Oxa-Michael 加成合成螺马酮 A 苯并类似物
DOI：
10.1021/acs.orglett.6b02328
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发表时间：
2016
期刊：
影响因子：
5.2
通讯作者：
T.
中科院分区：
文献类型：
--
作者：
Tsukamoto;H.; Hanada;S.; Kumasaka;K.; Kagaya;N.; Izumikawa;M.; Shin-ya;K.; Doi;T.
合成了两种与天然产物具有相同氧化态和不饱和度的碳原子的细胞毒性螺马酮A的苯并类似物，并对其进行了生物学评价。由1,3-环戊二酮衍生的α，α ' -二氧基烯二硫缩醛与受保护的（2-甲酰苯基）溴化镁和1,8-二羟基萘取代，然后进行脱保护，通过分子内醛醇反应生成这些类似物。苯并类似物和合成中间体对宫颈癌HeLa细胞的细胞毒性表明，4-环戊烯-1,3-二酮部分的生物活性是必要的。
Two benzo analogues of cytotoxic spiromamakone A, comprising carbon atoms with the same oxidation state and unsaturation degree as those of the natural products, are synthesized and biologically evaluated. Substitution of α,α′-dioxoketene dithioacetals, derived from 1,3-cyclopentanediones with protected (2-formylphenyl)magnesium bromide and 1,8-dihydroxynaphthalene, followed by deprotection, generated these analogues via an intramolecular aldol reaction. The cytotoxicity of benzo analogues and synthetic intermediates against cervical carcinoma HeLa cells shows the necessity of the 4-cyclopentene-1,3-dione moiety for biological activity.