A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction

Ibrahim Ali , Noorbatcha (2004) A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction. Tetrahedron, 60 (51). pp. 11733-11742. ISSN 0040-4020

PDF (A tandem highly steroselective FeCl3-promoted synthesis of a bisindoline: synthetic utility of radical cations in heterocyclic construction) - Published Version Restricted to Registered users only Download (1MB) | Request a copy

Abstract

A conceptually distinctive stereoselective construction of the novel dimer, N-[N'-acetyl-7,7'-bis-(3,4-dimethoxy-phenyl)-7,8,7',8'-tetrahydro-N'H-[8,8']biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)-indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AMI calculations. Mechanistic interpretations, consistent with our results, are discussed.

Item Type:	Article (Journal)
Additional Information:	3704/34910
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Engineering > Department of Biotechnology Engineering
Depositing User:	Prof. Dr. Ibrahim Ali Noorbatcha
Date Deposited:	20 Feb 2014 09:27
Last Modified:	20 Feb 2014 09:27
URI:	http://irep.iium.edu.my/id/eprint/34910

Actions (login required)

View Item