Abstract
A convenient optically active synthesis of (3a S,5 R,6a R)-5-hydroxy-hexahydrocyclopenta[ b]furan, a high-affinity nonpeptidyl ligand for HIV-1 protease inhibitor 2, is described. The synthesis utilizes commercially available (1 R,5 S)-(+)-2-oxabicyclo[3.3.0]oct-6-en-3-one as the starting material and oxymercuration or bromohydrin reaction as the key step. Enantiopure ligand was converted to protease inhibitor 2.
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