Silver- and gold-mediated intramolecular cyclization to substituted tetracyclic isoquinolizinium hexafluorostilbates

Fang Liu; Xiao Ding; Lei Zhang; Yu Zhou; Linxiang Zhao; Hualiang Jiang; Hong Liu

doi:10.1021/jo1006174

Silver- and gold-mediated intramolecular cyclization to substituted tetracyclic isoquinolizinium hexafluorostilbates

J Org Chem. 2010 Sep 3;75(17):5810-20. doi: 10.1021/jo1006174.

Authors

Fang Liu¹, Xiao Ding, Lei Zhang, Yu Zhou, Linxiang Zhao, Hualiang Jiang, Hong Liu

Affiliation

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.

PMID: 20684505
DOI: 10.1021/jo1006174

Abstract

A convenient route for the synthesis of various charged tetracyclic isoquinolizinium hexafluorostilbates was developed using AgSbF(6)/AuCl(PPh(3)) for the intramolecular addition of amine to alkyne. The described process is tolerant of a variety of functional groups and broadens the diversity of substrates with the use of 8-substituted tetracyclic isoquinolizinium salts.

Publication types

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

MeSH terms

Alkynes / chemistry
Amines / chemistry
Antimony / chemistry*
Cyclization
Gold / chemistry*
Isoquinolines / chemistry*
Molecular Structure
Organometallic Compounds / chemical synthesis*
Organometallic Compounds / chemistry
Silver / chemistry*
Stereoisomerism

Substances

Alkynes
Amines
Isoquinolines
Organometallic Compounds
Silver
Gold
Antimony