title: Synthesis of a 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone.
abstract: In order to develop an immunoassay of 7β-hydroxy-epiandrosterone, a stereoselective synthesis of a specific hapten, 7β-hydroxy-19-oxo-androstan 19-(O-carboxymethyl)oxime (17), was performed. This synthesis was achieved in 16% overall yield starting from the well-known 3β-acetoxy-19-hydroxy-5-androsten-17-one (1). After coupling of the alkyl oxime moiety, an allylic oxidation of the C-7 carbon under mild conditions followed by two selective reductions established all the functionalities of the final compound 17.
authors.forename: Clotilde
authors.initials: C
authors.lastname: Ferroud
authors.forename: Gilbert
authors.initials: G
authors.lastname: Revial
authors.forename: Christophe
authors.initials: C
authors.lastname: Ricco
authors.forename: Olivier
authors.initials: O
authors.lastname: Hennebert
authors.forename: Robert
authors.initials: R
authors.lastname: Morfin