Synthesis of angucyclines .8. Biomimetic-type synthesis of rabelomycin, tetrangomycin, and related ring B aromatic angucyclinones
Synthesis of angucyclines .8. Biomimetic-type synthesis of rabelomycin, tetrangomycin, and related ring B aromatic angucyclinones
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DOI：
10.1021/jo9622587
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发表时间：
1997-04-18
影响因子：
3.6
通讯作者：
Freund, C
中科院分区：
文献类型：
--
作者：
Krohn, K;Boker, N;Freund, C
具有芳环B的angucyclinones（1a-c和2a-c）在仿生类型的合成中通过从取代的萘醌12 a-c开始的两个连续的羟醛环化反应来合成。在两个环化步骤中，潜在亲核中心的C-H酸性决定了在动力学控制条件下的环化模式。在用过量NMO处理时，四氢蒽醌13 a-c/14 a-c在C-4处羟基化为酚蒽醌16 a-c。
The angucyclinones with aromatic ring B (1a-c and 2a-c) are prepared-in a biomimetic-type synthesis by two successive aldol cyclizations starting from the substituted naphthoquinones 12a-c. In both cyclization steps the C-H acidity of the potential nucleophilic centers determines the mode of cyclization under kinetically controlled conditions, The tetrahydroanthraquinones 13a-c/14a-c are hydroxylated at C-4 to the phenolic anthraquinones 16a-c upon treatment with excess NMO.