Syntheses of Steroid O-(3-Carboxypropyl)oximes

Abstract

The syntheses of O-(3-carboxypropyl)oxime derivatives, i.e. bis-homologues of O-(carboxymethyl)oxime derivatives (CMO), derived from dehydroepiandrosterone, testosterone and estradiol are presented. Both the reaction of steroid ketone with O-(3-carboxypropyl)hydroxylamine, and the reaction of sodium salt of steroid oxime with ethyl 4-bromobutyrate were alternatively evaluated, together with some other methods using successive chain lengthening. The compatibility with acetyl and methoxymethyl protecting groups was studied.