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Communication | Special issue | Vol 30, No. 1, 1990, pp.267-270
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S28
■ R-(+)- and S-(—)-Tetrahydroharmine: Preparation of Optically Pure Alkaloids and Acid-Catalyzed Racemization

Linda A. Chrisey and Arnold Brossi*

*Section of Medicinal Chemistry, Laboratory of Bioorganic Chrmistry, NIDDK, National Institute of Health, Bethesda, MD 20892, U.S.A.

Abstract

Chemical resolution of (+)-tetrahydroharmine (2) with optically active 10-camphorsulfonic acids afforded 1R-(+)-tetrahydroharmine (3A) as well as the 1S-(-)-isomer, 3B. Hplc analysis of ureas obtained by reaction with 1R-(+)-(1-phenylethyl)isocyanate demonstrated that the bases were greater than 98% optically pure. Racemization of 3A occurred in acidic solutions.