铜催化碘代色氨酸的环化反应：吡咯并吲哚的直接合成

Copper-catalyzed cyclization of iodo-tryptophans: a straightforward synthesis of pyrroloindoles.

作者信息

Coste Alexis, Toumi Mathieu, Wright Karen, Razafimahaléo Vanessa, Couty François, Marrot Jérome, Evano Gwilherm

机构信息

Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France.

出版信息

Org Lett. 2008 Sep 4;10(17):3841-4. doi: 10.1021/ol8015513. Epub 2008 Aug 6.

DOI:10.1021/ol8015513

PMID:18681449

Abstract

Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3- b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.

摘要

吡咯并吲哚是在大量生物活性生物碱中发现的关键结构基序。易于获得的2-碘色氨酸衍生物的分子内铜催化偶联反应产率极高，可得到多种多取代的对映体富集的四氢吡咯并[2,3-b]吲哚。二酮哌嗪也是这种环化反应的合适底物，这为构建四到七元多环体系提供了一条直接的途径。