利用亲碳路易斯酸催化的氢酰胺化反应和氧化傅克环化反应简洁合成四氢异喹啉生物碱的CDE环系

Concise synthesis of the CDE ring system of tetrahydroisoquinoline alkaloids using carbophilic Lewis acid-catalyzed hydroamidation and oxidative Friedel-Crafts cyclization.

作者信息

Obika Shingo, Yasui Yoshizumi, Yanada Reiko, Takemoto Yoshiji

机构信息

Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

出版信息

J Org Chem. 2008 Jul 4;73(13):5206-9. doi: 10.1021/jo800898k. Epub 2008 Jun 5.

DOI:10.1021/jo800898k

PMID:18529080

Abstract

A concise synthesis of the CDE ring system of the tetrahydroisoquinoline antitumor alkaloids such as saframycins, renieramycins, and ecteinascidins has been developed. Both Au(I)-catalyzed intramolecular hydroamidation of alkynylamide and NBS-mediated oxidative Friedel-Crafts cyclization of the resulting 2-ketopiperazine were utilized as key reactions.

摘要

已经开发出一种简洁的合成四氢异喹啉类抗肿瘤生物碱（如沙弗霉素、海兔霉素和埃博霉素）的CDE环系统的方法。炔基酰胺的金（I）催化分子内氢酰胺化反应以及由此产生的2-酮哌嗪的NBS介导的氧化傅克环化反应均被用作关键反应。