Tetrahedron p. 1711 - 1717 (2003)
Update date:2022-08-05
Topics:
Di Filippo, Marcello
Izzo, Irene
Savignano, Loredana
Tecilla, Paolo
De Riccardis, Francesco
The synthesis of the C2-symmetric bis-(20S)-5α-23,24-bisnorchol-16-en-3β,6α,7β-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-3β-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.
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