Summary
The absolute configuration of a novel chiral neuroleptic agent SU 23397 (I) was determined by ORD comparison of (+)-5-methoxy dihydro coumarilic acid (VIII), a synthetic precursor of SU 23397 (I), with (+)-dihydro coumarilic acid, whose absolute configuration is known9. This assignment was confirmed by oxidative degradation of (+)-5-methoxy dihydro coumarilic acidVIII tod-(+)-malic acid.
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B. M. Angrist, G. Sathananthan, H. Thompson and S. Gershon, Curr. Ther. Res.18, 359 (1975).
D. H. Mielke, D. M. Gallant, G. Bishop and C. M. Kessler, Psychopharmac. Commun.1, 117 (1975).
T. J. Petcher, J. Schmutz, H. P. Weber and T. G. White, Experientia31, 1389 (1975).
W. Lippmann, T. Pugsley and J. Merker, Life Sci.16, 213 (1975).
C. F. Huebner, U. S. Pattent 3,759,927 (to Ciba-Geigy).
D. M. Bowen, J. I. DeGraw, Jr, V. R. Shah and W. A. Bonner, J. med. Chem.6, 315 (1963).
W. A. Bonner, N. I. Burke, W. E. Fleck, R. K. Hill, J. A. Joule, B. Sjöberg and L. H. Zalkow, Tetrahedron20, 1419 (1964).
S. Tanaka, J. Am. chem. Soc.73, 872 (1951).
B. Sjöberg, Ark. Kemi15, 451 (1960).
G. Schmidt and H. Rosenkranz, Justus Leibigs Ann. Chem.1976, 124.
N. Finch, R. Dziemian, J. Cohen and B. G. Steinetz, Experientia31, 1002 (1975).
R. S. Cahn, C. K. Ingold and V. Prelog, Angew. Chem. Int. Ed.5, 385 (1966).
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Acknowledgments. We wish to acknowledge and thank Dr J. Karliner, Ciba-Geigy Corporation, Ardsley, New York, for the ORD curves. We thank Dr Max Wilhelm for support and encouragement.
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Chaudhuri, N.K., Ball, T.J. & Finch, N. The absolute configuration of SU 23397: A novel neuroleptic agent. Experientia 33, 575–577 (1977). https://doi.org/10.1007/BF01946504
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DOI: https://doi.org/10.1007/BF01946504