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Paper | Regular issue | Vol 26, No. 5, 1987, pp.1291-1302
Published online, 1st January, 1970
DOI: 10.3987/R-1987-05-1291
Synthesis and Determination of the Absolute Stereochemistry of the Enantiomers of 3-Substituted 1,2,3,4-Tetrahydroisoquinolines Related to the Calcium Antagonist Verapamil

Robin D. Clark, Jacob Berger, Chi-Ho Lee, and Joseph M. Muchowski

*Institute of Organic Chemistry, Syntex Discovery Research, 3401 Hillview Avenue, Palo Alto, California 94304, U.S.A.

Abstract

The four stereoisomers of 3-[4-cyano-4-(3,4-dimethoxypheny1)- 5-methylhex-l-yl]-1,2,3,4-tetrahydro-6,7dimethoxy-2-methylisoquinoline (2) were prepared. The stereochemistry of the side chain quaternary carbon was derived from iodide 4 of known absolute configuration. The absolute stereochemistry at the 3-position of the tetrahydroisoquinoline was determined by correlation with L-DOPA. These compounds are related to the calcium antagonist verapamil and the calcium antagonist activity was greatest for the (3S,4S) isomer.