A facile synthesis of 2-benzyloxy/2-(4-isopropylbenzyloxy)-2-methyl-3-(4- substituted phenyl)propanoic acid based insulin sensitizing agents: RSR 13-15 and PKR13-15

Article abstract of DOI:10.1007/s00044-004-0109-4

The title compounds (RSR_13-15) and (PKR_13-15) were prepared by the etherification of benzyl alcohol and 4-isopropylbenzyl alcohol respectively with ethyl-2-bromo-2-methyl-3-(4-substituted phenyl)propanoates in the presence of sodium hydride in THF followed by alkaline hydrolysis of the ethyl esters. The substituted propanoic acids used in this synthetic sequence were prepared by magnesium-methanol reduction of correspondingly substituted propenoic acids, which in turn were prepared via 'Perkin Reaction' of 4-substituted benzaldehydes with propanoic anhydride. The details of the synthetic sequence followed for the preparation of all these compounds having almost all the structural features required for a compound to act as a potent insulin sensitizing agent are reported. Birkhaeuser Boston 2004.