IMPROVED METHODS FOR THE REDUCTIVE ALKYLATION OF METHOXYBENZOIC ACIDS AND ESTERS: APPLICATION TO THE SYNTHESIS OF BICYCLIC KETONES

Article abstract of DOI:10.1016/S0040-4020(01)90577-0

A series of methoxybenzoic acids and esters was reduced by metal-ammonia solutions and the resulting 1,4-dihydro products were either alkylated subsequently.Three different types of alkyl iodies were employed to introduce the elements of a butanone or pentanone side-chain as a prelude to adding a fused six-membered ring, thereby completing the preparation of several analogues of the Wieland-Miescher ketone 4a in which the angular substituent was oxygenated.