Abstract: Using Pictet-Spengler condensation, ammonification, methylation, dehydration and decyanation, N^b-methyl-tetrahydroharman and the synthetic intermediates 1S,S、1S,R、2S,S、2S, R、3S,S、3S,R、4S,S、4S, R were obtained. Their ¹H NMR spectra were assigned based on COSY spectroscopy and their configurations of 1-C were determined by NOE experiments. It was shown that for all of the S, S isomers there were NOE relationships between 1-H and 3-H and for all of the S, R isomers NOE relationships between 1-CH₃ and 3-H. Based on the results of NOE and the help of Dreiding stereomodels their conformations were discussed.

Key words: N^b-methyl-tetrahydroharman, Stereochemistry, 2D NMR