The use of L-(+)-tartaric acid in the enantioselective synthesis of isoquinoline alkaloids

Tetrahedron Letters

Volumn 41, Issue 12, 2000, Pages 1963-1966

  Ziólkowski, Marek ^a   Czarnocki, Zbigniew ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

Alkaloids; Asymmetric synthesis; Hydroxy acids; Isoquinolines

Indexed keywords

ISOQUINOLINE DERIVATIVE; N ACETYLCALYCOTOMINE; TARTARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; STRUCTURE ANALYSIS;

EID: 0142070603     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00072-1     Document Type: Article

References (9)

1. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1995; p. 940.
2. Inomata, K.; Ukaji, Y. Rev. Heteroatom. Chem. 1998, 18, 119-140.
3. Lee, J. Y.; Lee, Y. S.; Chung, B. Y.; Park, H. Tetrahedron 1997, 53, 2449-2458.
4. Dörnyei, G.; Szantay, Cs. Acta Chim. Acad. Sci. Hung. 1976, 89, 161-168.
5. Czarnocki, Z.; Suh, D.; MacLean, D. B.; Hultin, P.G.; Szarek,W. A. Can. J. Chem. 1991, 70, 1555-1561 and references cited therein.
6. +; 460 (18); 234 (100).
7. 8.
8. Czarnocki, Z.; Ziólkowski, M.; Leniewski, A.; Maurin, J. K. Enantiomer 1999, 4, 71-77 and references cited therein.
9. 19F NMR spectra, a pair of signals (due to the presence of stable conformers) were observed at -71.18 and -71.54 ppm (S enantiomer) with relative intensities 1.00:2.32, R enantiomer was not observed. Therefore, the enantiomeric purity of (S)-(-)-N-acetylcalycotomine 11 exceeds the value of 98% ee.