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通过 - 硅基、- 烯酮缩醛与炔烃的环化反应合成二氢吡啶酮及其在菲并吲哚里西啶生物碱简洁全合成中的应用。

Annulation of -silyl ,-ketene acetals with alkynes for the synthesis of dihydropyridinones and its application in concise total synthesis of phenanthroindolizidine alkaloids.

作者信息

Lee Seokwoo, Shin Jae Eui, Yoon Ran, Yoo Hanbin, Kim Sanghee

机构信息

College of Pharmacy, Seoul National University, Seoul, Republic of Korea.

College of Pharmacy, Chungnam National University, Daejeon, Republic of Korea.

出版信息

Front Chem. 2023 Sep 21;11:1267422. doi: 10.3389/fchem.2023.1267422. eCollection 2023.

DOI:10.3389/fchem.2023.1267422
PMID:37810583
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10551152/
Abstract

The formation of -heterocycles with multiple substituents is important in organic synthesis. Herein, we report a novel method for the construction of functionalized dihydropyridinone rings through the annulation of an amide -carbon with a tethered alkyne moiety. The reaction of the amide with the alkyne was achieved via -silyl ,-ketene acetal formation and silver-mediated addition. Furthermore, the developed method was applied for the total synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids. By varying the coupling partners, a concise and collective total synthesis of these alkaloids was achieved.

摘要

构建具有多个取代基的杂环在有机合成中具有重要意义。在此，我们报道了一种通过酰胺碳与连接的炔烃部分环化构建功能化二氢吡啶酮环的新方法。酰胺与炔烃的反应通过硅基烯酮缩醛的形成和银介导的加成实现。此外，所开发的方法被应用于菲并吲哚里西啶和菲并喹诺里西啶生物碱的全合成。通过改变偶联伙伴，实现了这些生物碱的简洁且集中的全合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/b4e16df59223/FCHEM_fchem-2023-1267422_wc_sch6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/f639f9bd76c1/FCHEM_fchem-2023-1267422_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/ce5133892896/fchem-11-1267422-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/f06c6b161a58/FCHEM_fchem-2023-1267422_wc_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/1ef2d2be1e55/FCHEM_fchem-2023-1267422_wc_sch3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/4594cff1a5d2/FCHEM_fchem-2023-1267422_wc_sch4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/2ce6e85c9154/FCHEM_fchem-2023-1267422_wc_sch5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/b4e16df59223/FCHEM_fchem-2023-1267422_wc_sch6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/f639f9bd76c1/FCHEM_fchem-2023-1267422_wc_sch1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/ce5133892896/fchem-11-1267422-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/f06c6b161a58/FCHEM_fchem-2023-1267422_wc_sch2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/1ef2d2be1e55/FCHEM_fchem-2023-1267422_wc_sch3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/4594cff1a5d2/FCHEM_fchem-2023-1267422_wc_sch4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/2ce6e85c9154/FCHEM_fchem-2023-1267422_wc_sch5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/185c/10551152/b4e16df59223/FCHEM_fchem-2023-1267422_wc_sch6.jpg

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本文引用的文献

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Palladium-catalyzed Synthesis of Fused Carbo- and Heterocycles.钯催化的稠合碳环和杂环化合物合成。
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Possible pharmaceutical applications can be developed from naturally occurring phenanthroindolizidine and phenanthroquinolizidine alkaloids.
可从天然存在的菲并吲哚里西啶和菲并喹诺里西啶生物碱开发出可能的药物应用。
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