Synthesis of dihydrooxepin models related to the antitumor antibiotic MPC1001
Synthesis of dihydrooxepin models related to the antitumor antibiotic MPC1001
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DOI：
10.1021/ol071147z
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发表时间：
2007-07-19
期刊：
影响因子：
5.2
通讯作者：
Clive, Derrick L. J.
中科院分区：
文献类型：
--
作者：
Peng, Jianbiao;Clive, Derrick L. J.
4-羟基-L-脯氨酸被转化为四氢氧杂[4,3-b]吡咯环系统，这是有效抗肿瘤剂 MPC1001 的特征。关键步骤是使用 Bredereck 试剂区域选择性形成插烯酰胺，并通过加成消除将醇酸诱导环化到该酰胺的碳-碳双键上，生成七元氧杂环亚基。
4-Hydroxy-L-proline was converted into the tetrahydrooxepino[4,3-b]pyrrole ring system characteristic of the potent antitumor agent MPC1001. Key steps were regioselective formation of a vinylogous amide by use of Bredereck's reagent and acid-induced cyclization of an alcohol onto the carbon-carbon double bond of that amide by addition-elimination to generate the seven-membered oxacyclic subunit.