Skip to Content
MilliporeSigma
  • A convergent approach to (R)-Tiagabine by a regio- and stereocontrolled hydroiodination of alkynes.

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

Organic & biomolecular chemistry (2010-06-10)
Giuseppe Bartoli, Roberto Cipolletti, Giustino Di Antonio, Riccardo Giovannini, Silvia Lanari, Mauro Marcolini, Enrico Marcantoni
ABSTRACT

The occurrence of unsaturated systems in natural products combined with the mildness and the wide range of applicability of CeCl(3) promoted methodologies suggest several potential future synthetic applications within the field of total synthesis of biologically active molecules. On this concept, the use of CeCl(3).7H(2)O-NaI system as an efficient heterogeneous promoter has been highlighted in the iodofunctionalization of carbon-carbon 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 , named (R)-Tiagabine, which is a potent and selective gamma-aminobutyric acid (GABA) uptake inhibitor with proven anticonvulsant efficacy in humans.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cerium(III) chloride heptahydrate, 99.9% trace metals basis
Sigma-Aldrich
Cerium(III) chloride heptahydrate, purum p.a., ≥98.0% (AT)
Sigma-Aldrich
Cerium(III) chloride heptahydrate, 99.999% trace metals basis
Sigma-Aldrich
Cerium(III) chloride, AnhydroBeads, −10 mesh, 99.9%
Sigma-Aldrich
Cerium(III) chloride, AnhydroBeads, −10 mesh, ≥99.99% trace metals basis