PREPARATION OF THE (R)-ENANTIOMER AND (S)-ENANTIOMER OF 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
L. Dubois et al., PREPARATION OF THE (R)-ENANTIOMER AND (S)-ENANTIOMER OF 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, Tetrahedron : asymmetry, 6(2), 1995, pp. 455-462
The preparation of both enantiomers of (R,S)-1, a novel, chiral benzod
iazepine 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 diaster
eomeric 5-N-(-)-menthylcarbamates. (S)-1 had a higher affinity for the
benzodiazepine receptor in vitro than (R)-1, demonstrating for the fi
rst time that beta-carbolines, like benzodiazepines, can also be recog
nized stereospecifically by this receptor.