THE SYNTHESIS OF GEM-CYCLOPENTYL SUBSTITUTED GLUTARATES VIA THE OXIDATIVE RING CONTRACTION OF 2-ACETYLCYCLOHEXANONES

ABSTRACT

A two step synthesis of differentially protected gem-cyclopentyl glutarates has been developed from 2-acetylcyclohexanone and acrylates. The key step involves an oxidative ring contraction reaction with hydrogen peroxide. The methodology has been used to prepare intermediates used in the preparation of the atriopeptidase inhibitor candoxatril.

Keywords:

• Oxidative ring-contraction
• Hydrogen peroxide
• Preparation of cyclopentyl substituted glutarates

Acknowledgment

We would like to thank Dr. Mike Williams (PGRD, Sandwich) for his encouragement and helpful discussions during this work.