Issue 15, 2010

A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

Abstract

The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl3 promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl3·7H2O–NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carboncarbon triple bonds. The study has shown that this method would be particularly interesting for the stereoselective formation of trisubstituted (Z)- or (E)-iodoalkenes by simply changing the nature of the solvent. The methodology has been successfully applied to the synthesis of (R)-1-[4,4-bis-(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid 1, named (R)-Tiagabine, which is a potent and selective γ-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans.

Graphical abstract: A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

Article information

Article type
Paper
Submitted
13 Apr 2010
Accepted
21 May 2010
First published
09 Jun 2010

Org. Biomol. Chem., 2010,8, 3509-3517

A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

G. Bartoli, R. Cipolletti, G. Di Antonio, R. Giovannini, S. Lanari, M. Marcolini and E. Marcantoni, Org. Biomol. Chem., 2010, 8, 3509 DOI: 10.1039/C005042C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements