Synthesis of the left-hand portion of geldanamycin using an anti glycolate aldol reaction.
Synthesis of the left-hand portion of geldanamycin using an anti glycolate aldol reaction.
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DOI：
10.1021/ol0068997
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发表时间：
2001-01
期刊：
影响因子：
5.2
通讯作者：
M. Andrus;E. Meredith;B. Sekhar
中科院分区：
文献类型：
--
作者：
M. Andrus;E. Meredith;B. Sekhar
本文报道了抗肿瘤天然产物安莎霉素的左边部分格尔德霉素的合成。一种高级中间体将甲氧基醌前体作为具有10个碳链的五取代苯掺入，所述10个碳链包含6个立构中心中的4个。关键反应是一个新的反羟乙酸酯羟醛缩合反应，其中一个新的二芳基-4-氧杂吡喃酮用于生成C-11，C-12羟基，甲氧基官能团。
[figure: see text] A synthesis of the left-hand portion of the ansamycin antitumor natural product geldanamycin is reported. An advanced intermediate incorporates the methoxyquinone precursor as a pentasubstituted benzene with a 10-carbon chain that contains 4 of the 6 stereocenters. The key reaction is a novel anti glycolate aldol reaction with a new diaryl-4-oxapyrone used to generate the C-11, C-12 hydroxy, methoxy functionality.