ASYMMETRIC SYNTHESIS OF (1S)-(-)-TRYPARGINE

Abstract

(1S)-(-)-Trypargine (1a) was synthesized from (1S, 3R)-(-)-2-benzyl-3-(methoxycarbonyl)-1, 2, 3, 4-tetrahydro-9H-pyrido [3, 4-b] indole-1-propionic acid (3a), prepared by the asymmetric Pictet-Spengler reaction of N_b-benzyl-(D)-tryptophan methyl ester (2) with α-ketoglutaric acid. The absolute configuration of natural trypargine (1a) at the C₁ position was determined to be the S-configuration.