Total Syntheses of Pleiocarpamine, Normavacurine, and C-Mavacurine.
Total Syntheses of Pleiocarpamine, Normavacurine, and C-Mavacurine.
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DOI：
10.1021/acs.orglett.9b01084
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发表时间：
2019-04
期刊：
影响因子：
5.2
通讯作者：
Keigo Sato;N. Kogure;M. Kitajima;H. Takayama
中科院分区：
文献类型：
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作者：
Keigo Sato;N. Kogure;M. Kitajima;H. Takayama
完成了c -马伐库林型吲哚类生物碱（±）- pleiocarparamine,（±）-normavacurine和（±）- c -马伐库尿的全合成。合成的关键步骤是在具有重氮功能的corynanth型化合物中C16位的金属羰基与N1位的环化。对于这种环化，使用胺-硼烷配合物对底物进行N4修饰是固定分子构象必不可少的。
The total syntheses of C-mavacurine-type indole alkaloids, (±)-pleiocarpamine, (±)-normavacurine, and (±)- C-mavacurine, were accomplished. The key step in the syntheses was the cyclization between the metal carbenoid at C16 and the N1 position in a Corynanthe-type compound that was equipped with a diazo function. For this cyclization, the N4 modification of the substrate using an amine-borane complex was indispensable to fix the molecular conformation.