New luminescent materials based on a steroid molecule

An efficient way to synthesize new steroid derivatives substituted in the A ring is described; based on a new route to stable diazo steroid 3-diazoand rosta-1,4-dien-17-one (4). Using the Barton-Kellogg olefination, it is poss ible to combine the steroid molecule with a heterocyclic substructure: the oxazoline ring system. Unlike the starting material, the resuiting oxazinyl idene products 2 are luminescence dyes with high quantum yields, and posses s Stokes shifts of about 100 nm. The described synthetic method opens the w ay for the development of new diagnostic and pharmaceutical materials conta ining a steroidal substructure.