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Issue 15, 2010
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A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes

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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

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Publication details

The article was received on 13 Apr 2010, accepted on 21 May 2010 and first published on 09 Jun 2010


Article type: Paper
DOI: 10.1039/C005042C
Citation: Org. Biomol. Chem., 2010,8, 3509-3517
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    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

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