Synthesis ( IF 2.2 ) Pub Date : 2018-12-13 , DOI: 10.1055/s-0037-1610673 Alexey Fedorov 1 , Ekaterina Shchegravina 1 , Elena Svirshchevskaya 2 , Hans-Günther Schmalz 3
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Abstract
A six-step semisynthetic approach towards chiral nonracemic pyrrolo-allocolchicinoids starting from naturally occurring colchicine was developed. The synthetic scheme includes an electrocyclic tropolone ring contraction to afford allocolchicinic acid followed by the Curtius reaction, giving the corresponding aniline. The Sandmeyer reaction and copper-mediated hydrazination gave hydrazine-substituted allocolchicine. This was introduced into the Fischer indole synthesis, affording libraries of regioisomeric indole-based allocolchicine congeners.
A six-step semisynthetic approach towards chiral nonracemic pyrrolo-allocolchicinoids starting from naturally occurring colchicine was developed. The synthetic scheme includes an electrocyclic tropolone ring contraction to afford allocolchicinic acid followed by the Curtius reaction, giving the corresponding aniline. The Sandmeyer reaction and copper-mediated hydrazination gave hydrazine-substituted allocolchicine. This was introduced into the Fischer indole synthesis, affording libraries of regioisomeric indole-based allocolchicine congeners.
中文翻译：
从天然秋水仙碱开始的非外消旋取代吡咯并分配的鬼臼类固醇的简便合成方法
摘要
从天然存在的秋水仙碱出发，开发了一种六步半合成方法，用于手性非外消旋吡咯并茂金属类化合物。合成方案包括环四环酮环收缩，得到二十碳五烯酸，然后进行库尔蒂斯反应，得到相应的苯胺。桑德迈尔反应和铜介导的酰肼化作用得到肼取代的二十碳五烯七胺。这被引入到Fischer吲哚合成中，提供了基于区域异构吲哚的allocolchicine同类物的文库。
从天然存在的秋水仙碱出发，开发了一种六步半合成方法，用于手性非外消旋吡咯并茂金属类化合物。合成方案包括环四环酮环收缩，得到二十碳五烯酸，然后进行库尔蒂斯反应，得到相应的苯胺。桑德迈尔反应和铜介导的酰肼化作用得到肼取代的二十碳五烯七胺。这被引入到Fischer吲哚合成中，提供了基于区域异构吲哚的allocolchicine同类物的文库。
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