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

Shingo Obika; Yoshizumi Yasui; Reiko Yanada; Yoshiji Takemoto

doi:10.1021/jo800898k

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

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

Authors

Shingo Obika¹, Yoshizumi Yasui, Reiko Yanada, Yoshiji Takemoto

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 18529080
DOI: 10.1021/jo800898k

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Antineoplastic Agents / chemical synthesis
Cyclization
Molecular Structure
Oxidation-Reduction
Tetrahydroisoquinolines / chemical synthesis*

Substances

Alkaloids
Antineoplastic Agents
Tetrahydroisoquinolines