Synthesis of Calycotomine via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents

Jung-Eun Yang; Jin-Kyung In; Mi-Sung Lee

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Synthesis of Calycotomine via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents

机译：通过N，O-缩醛TMS醚的Pictet-Spengler型反应以N-酰基亚胺离子当量的方式合成Catocotomine

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摘要

An efficient Pictet-Spengler type reaction of N,O-acetal TMS ethers for the practical synthesis of 1-substituted tetrahydroquinolines,medicinally important alkaloids,has been accomplished.To demonstrate the versatility of this novel procedure,the total synthesis of calycotomine,a representative 1-hydroxymethyl substituted tetrahydroisoquinohne,is also described.

机译：N，O-乙缩醛TMS醚的有效Pictet-Spengler型反应可用于实际合成1-取代的四氢喹啉，医学上重要的生物碱。还描述了1-羟甲基取代的四氢异喹啉。

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《Bulletin of the Korean Chemical Society》 |2007年第8期|共4页
作者
Jung-Eun Yang; Jin-Kyung In; Mi-Sung Lee;
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正文语种 eng
中图分类化学工业;
关键词
Tetrahydroisoquinoline; Pictet-Spengler reaction; N; O-Acetal TMS ether; Alkaloid;

机译：四氢异喹啉;Pictet-Spengler反应;N;O-缩醛TMS醚;生物碱;

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专利

1. Synthesis of Calycotomine via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents [J] . Jung-Eun Yang, Jin-Kyung In, Mi-Sung Lee Bulletin of the Korean Chemical Society . 2007,第8期

机译：通过N，O-缩醛TMS醚的Pictet-Spengler型反应以N-酰基亚胺离子当量的方式合成Catocotomine
2. Stereoselective Formation of N-Acyliminium Ion via Chiral N,O-Acetal TMS Ether and Its Application to the Synthesis of B-Amino Acids [J] . Dong-Yun Shin, Jae-Kyung Jung, Seung-Yong Seo, Organic letters . 2003,第20期

机译：通过手性N，O-缩醛TMS醚立体选择性地形成N-酰基亚胺离子及其在合成B-氨基酸中的应用
3. cis-Dihydroxylated alpha-Trifluoromethylated N,O-Acetal from L-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions [J] . Ben Jamaa Abdelkhalek, Latrache Mohammed, Riguet Emmanuel, The Journal of Organic Chemistry . 2020,第15期

机译：来自L-酒石酸的顺式二羟基化α-三氟甲基化N，O-缩醛：通过N-酰胺离子的非对映选择性象形型 - Spengler环化合成四氢立体封闭体
4. The solid-phase intramolecular N-acyliminium Pictet-Spengler reaction as a crossroad to a plethora of novel heterocyclic peptides [C] . Thomas E.Nielsen, Morten Meldal International Peptide Symposium;European Peptide Symposium . 2005

机译：固相的分子内N-酰基亚胺氨基乙基纤维素 - Spengler作为十字路口到多种新型杂环肽的十字路口
5. I. Enantioselective total synthesis of quinine and quinidine. II. Thiourea-catalyzed enantioselective C-C bond-forming reactions. a. Catalytic asymmetric N-acyliminium ion cyclizations. b. Catalytic asymmetric aza-Baylis-Hillman reactions [D] . Raheem, Izzat Tiedje 2008

机译：I.奎宁和奎尼丁的对映选择性全合成。二。硫脲催化的对映选择性C-C键形成反应。一个。催化不对称N-酰亚胺离子环化。 b。催化不对称氮杂-Baylis-Hillman反应
6. A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins [O] . Nianhong Lu, Lihong Wang, Zhanshan Li, 2012

机译：通过N-酰基亚胺离子与未活化烯烃的分子间偶联反应简明合成3-（1-烯基）异吲哚啉-1-酮和5-（1-烯基）吡咯-2-酮
7. Synthesis of Calycotomine via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents [O] . Jung-eun Yang, Jin-kyung In, Mi-sung Lee, 2007

机译：通过pictet-spengler型反应合成Calycotomine N，O-乙缩醛Tms醚作为N-酰基亚胺离子等价物

Synthesis of Calycotomine via Pictet-Spengler Type Reaction of N,O-Acetal TMS Ethers as N-Acyliminium Ion Equivalents

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