A stereoselective synthesis of 1 alpha-(3'-carboxypropyl)-4-androsten-17 beta-ol-3-one: Preparation of immunoreagents for quantification of testosterone by fluorescence polarization immunoassay

1 alpha-(3'-Carboxypropyl)-4-androsten-17 beta-ol-3-one (2), a novel hapten, was prepared from boldenone (3) via addition of 4-pentenyl magnesium bromide in the presence of CuBr, as a key step in >95% epimeric excess and 13.8% overall yield Two immunogens (7,8) and three fluorescent tracers (11,18,19) were prepared from acid (2) for the development of an immunoassay for testosterone (1). (C) 1997 Elsevier Science Ltd.