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Communication | Special issue | Vol 59, No. 2, 2003, pp.521-526
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S87
■ Synthesis and CD Measurement of Chiral 1-Ethyl-3-carboxy-1,2,3,4-tetrahydro-β-carbolines: C1 Configuration and Second Sphere Chirality

Masashi Yokoya, Kyohei Masubuchi, Mariko Kitajima, Hiromitsu Takayama, and Norio Aimi*

*Graduate School of Pharmaceutical Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Chiral diastereomers, (1S)-ethyl-(3S)-carboxy-1,2,3,4-tetrahydro- β-carboline and (1R)-ethyl-(3S)-carboxy-1,2,3,4-tetrahydro-β-carboline, were synthesized. Complete 1H and 13C NMR spectral assignments were made and the C-ring conformations were clarified by NMR spectral measurements and DFT potential energy calculation using the 6-31G(d) basis set. CD spectra were measured and the 1Lb band Cotton effects were found to be controlled by both the C1 absolute configuration and the C-ring conformation.