Modular Synthesis of the Pentacyclic Core of Batrachotoxin and Select Batrachotoxin Analogue Designs.
Modular Synthesis of the Pentacyclic Core of Batrachotoxin and Select Batrachotoxin Analogue Designs.
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DOI：
10.1039/c2sc21723f
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发表时间：
2013-03-01
期刊：
影响因子：
8.4
通讯作者：
Bois JD
中科院分区：
文献类型：
--
作者：
Devlin AS;Bois JD
有效的电压门控钠离子通道激动剂巴曲霍毒素的五环类似物可以通过中间体呋喃与双烯亲环分子进行Diels-Alder环加成反应来获得。3-溴呋喃作为1，2-二阴离子的等价物的使用，氨基甲酸酯还原N-烷基化反应在同型吗啉环组装中的应用，以及脑脊液作为一种有效的试剂来生成苯炔、环己炔和相关的双烯亲和剂，这些都强调了这项工作。
Pentacyclic analogues of the potent voltage-gated sodium ion channel agonist batrachotoxin can be accessed through an intermediate furan by exploiting Diels-Alder cycloaddition reactions with ring-strained dienophiles. The use of 3-bromofuran as a 1,2-dianion equivalent, the application of carbamate reductive N-alkylation for homomorpholine ring assembly, and the demonstration of CsF as an effective reagent for generating benzyne, cyclohexyne, and related dienophiles underscore this work.