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将手性池方法应用于稀有的生物活性菲并喹嗪生物碱的噻吩类似物。

Use of chiral-pool approach into -thieno analogues of the scarce bioactive phenanthroquinolizidine alkaloids.

作者信息

Šafář Peter, Marchalín Štefan, Prónayová Nadežda, Vrábel Viktor, Lawson Ata Martin, Othman Mohamed, Daïch Adam

机构信息

Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovak Republic.

Central Laboratories, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovak Republic.

出版信息

Tetrahedron. 2016 Jun 9;72(23):3221-3231. doi: 10.1016/j.tet.2016.04.047. Epub 2016 Apr 21.

DOI:10.1016/j.tet.2016.04.047
PMID:32287429
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7111795/
Abstract

The stereoselective synthesis of -thieno analogues of the phenanthroquinolizidine bioactive alkaloids (-)-Cryptopleurine and (-)-(15)-Hydroxycryptopleurine was achieved in five steps starting from easily available enantiopure ()-2-aminoadipic acid used as chiral pool and nitrogen atom source. During these investigations, both π-cationic cyclization of chiral -thienylmethyl-6-oxopipecolinic acids into pure ()-keto-lactams and theirs regioselective and diastereoselective reduction, considered as key steps of this sequence, were studied. Of particular interest, the Friedel-Crafts cyclization using (CFCO)O/BF·EtO show that near the expected keto-lactams, enamides and enamidones containing trifluoromethyl residue were isolated. A mechanism leading to the latter products with high synthetic potential was discussed.

摘要

从易于获得的对映体纯的（）-2-氨基己二酸作为手性库和氮原子源开始，通过五步反应实现了菲并喹嗪类生物活性生物碱（-）-隐品碱和（-）-（15）-羟基隐品碱的噻吩类似物的立体选择性合成。在这些研究中，研究了手性噻吩基甲基-6-氧代哌啶酸的π-阳离子环化生成纯的（）-酮内酰胺及其区域选择性和非对映选择性还原，这被认为是该序列的关键步骤。特别值得注意的是，使用（CFCO）O/BF·EtO进行的傅克环化反应表明，在预期的酮内酰胺附近，分离出了含有三氟甲基残基的烯酰胺和烯胺酮。讨论了导致具有高合成潜力的后一种产物的机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/7d15963183a1/sc7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/1f12277d6e61/fx1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/23f1d85d8509/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/ddc6f0d9e704/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/e873e2944f60/sc4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/86d408ae35a4/sc5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/81cb59770f42/sc6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/79e19769d958/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/7d15963183a1/sc7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/1f12277d6e61/fx1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/9023a671a7d5/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/23f1d85d8509/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/ddc6f0d9e704/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/e873e2944f60/sc4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/86d408ae35a4/sc5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/81cb59770f42/sc6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/79e19769d958/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a5bc/7111795/7d15963183a1/sc7.jpg

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