The synthesis of the C-2-symmetric bis-(20S)-5alpha-23,24-bisnorchol-16-en-3beta,6alpha,7beta-triol-22-terephthaloate (1), active as Na+-transporting transmembrane channel, has been achieved in 16 steps (10% overall yield) starting from the commercially available androst-5-en-3beta-ol-17-one (3). The straightforward stereospecific functionalization of the side-chain, via the 'ene' reaction, and the successful regioselective terephthaloylation of the C-22 hydroxy group, illustrate the efficiency of the synthetic strategy.
