使用 Pd 催化的级联环化和 Rh 催化的氨甲酰化反应构建 Dragmacidin E 的核心结构的综合研究。

Synthetic Study of Dragmacidin E: Construction of the Core Structure Using Pd-Catalyzed Cascade Cyclization and Rh-Catalyzed Aminoacetoxylation.

机构信息

Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.

Molecular Chirality Research Center, Chiba University , 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.

出版信息

J Org Chem. 2017 Mar 3;82(5):2787-2793. doi: 10.1021/acs.joc.7b00083. Epub 2017 Feb 23.

DOI:10.1021/acs.joc.7b00083

PMID:28217992

Abstract

We developed a novel synthetic method of the core structure of dragmacidin E bearing a 7-membered ring-fused bis(indolyl)pyrazinone skeleton. Formation of the 7-membered ring-fused tricyclic indole skeleton was accomplished using a palladium-catalyzed Heck insertion-allylic amination cascade. Vicinal difunctionalization of the 7-membered ring was realized via a rhodium-catalyzed aminoacetoxylation.

摘要

我们开发了一种新的含有 7 元环稠合双（吲哚基）吡嗪酮骨架的 Dragmacidin E 核心结构的合成方法。该 7 元环稠合三环吲哚骨架的形成是通过钯催化 Heck 插入-烯丙基胺化级联反应完成的。通过铑催化的氨乙酰氧基化反应实现了 7 元环的邻二官能化。