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Paper | Regular issue | Vol 34, No. 3, 1992, pp.483-495
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5912
Stereospecific Synthesis of trans, cis-1,3,4-Trisubstituted 1,2,3,4-Tetrahydro-β-Carbolines

Mohammad Behforouz,* Sarah J. West, Chitra Chakrabarty, David A. Rusk, and Hamideh Zarrinmayeh

*Department of Chemistry, Ball State University, Muncie, IN 47306, U.S.A.


Pictet-Spengler condensation of Nb-benzyl-β-methyltryptophan methyl ester (2RS, 3SR;4) with aldehydes followed by debenzylation afforded trans, cis-1,3,4-trisubstituted 1,2,3,4-tetrahydro-β-carbolines in complete stereospecific fashion. Tetrahydro-β-carbolines (6a) and (6b) were prepared by the direct condensation of β-methyltryptophan methyl ester (4) with the corresponding aldehydes. The stereochemistry of the products was confirmed by an X-ray analysis of 6a.