PREPARATION OF THE (R)-ENANTIOMER AND (S)-ENANTIOMER OF 10-HYDROXYMETHYLFURO[3,4-C]-BETA-CARBOLINE-2(10H)ONE, THE FIRST EXAMPLE OF A BENZODIAZEPINE RECEPTOR-LIGAND OF THE BETA-CARBOLINE FAMILY HAVING A STEREOGENIC CENTER

The preparation of both enantiomers of (R,S)-1, a novel, chiral benzodiazepine receptor ligand of the beta-carboline family, using (R)- and (S)-D-glyceraldehyde as sources of chirality, is described. Racemic (R,S)-1 was also resolved by chromatographic separation of their diastereomeric 5-N-(-)-menthylcarbamates. (S)-1 had a higher affinity for the benzodiazepine receptor in vitro than (R)-1, demonstrating for the first time that beta-carbolines, like benzodiazepines, can also be recognized stereospecifically by this receptor.