Synthesis 2014; 46(23): 3221-3228
DOI: 10.1055/s-0034-1378616
paper
© Georg Thieme Verlag Stuttgart · New York

A New Synthetic Route Towards Aliskiren Intermediates

Authors

  • Franc Požgan

    a   Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
  • Bogdan Štefane*

    a   Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, 1000 Ljubljana, Slovenia
  • Davor Kiđemet

    b   Krka, Pharmaceutical company, d.d., Novo mesto, Šmarješka cesta 6, 8501 Novo mesto, Slovenia   Fax: +386(1)2419220   Email: bogdan.stefane@fkkt.uni-lj.si
  • Janez Smodiš

    b   Krka, Pharmaceutical company, d.d., Novo mesto, Šmarješka cesta 6, 8501 Novo mesto, Slovenia   Fax: +386(1)2419220   Email: bogdan.stefane@fkkt.uni-lj.si
  • Rok Zupet

    b   Krka, Pharmaceutical company, d.d., Novo mesto, Šmarješka cesta 6, 8501 Novo mesto, Slovenia   Fax: +386(1)2419220   Email: bogdan.stefane@fkkt.uni-lj.si
Further Information

Publication History

Received: 14 May 2014

Accepted after revision: 18 July 2014

Publication Date:
21 August 2014 (online)


Graphical Abstract

Abstract

The synthesis of aliskiren intermediates was accomplished by attaching the 3,4-dialkoxyphenyl unit to precursor C-8 lactone-carboxylic acid derivatives using organometallic reagents. Totally different reactivities of the lactone-carboxylic acid chloride substrate towards organomagnesium and organoboron reagents were observed.