Stereospecific Synthesis of a Novel Farnesyl Protein Transferase Inhibitor, Valinoctin A and Its Analogues
1996 Volume 49 Issue 10 Pages 1031-1035
Details
1996 Volume 49 Issue 10 Pages 1031-1035
(2S, 3R)-3-Amino-2-hydroxyoctanoic acid was synthesized by Curtius rearrangement of an azide derivative of (S)-malic acid. Total syntheses of valinoctin A and its analogues were achieved by a coupling of (2S, 3R)-3-amino-2-hydroxyoctanoic acid moiety with L-valine or several other amino acids moieties. 2S configuration of 3-amino-2-hydroxyoctanoic acid moiety was found to be important for the inhibitory activity and the L-valine moiety of valinoctin A was exchangeable with other L-amino acids.
