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.
Synthesis of a Transmembrane Ionophore Based on a C2 Symmetric Polyhydroxysteroid Derivative
TECILLA, PAOLO;
2003-01-01
Abstract
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.File in questo prodotto:
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