Acid-catalysed C-3 epimerization of reserpine and other indolo[2,3-a]quinolizidines

Heterocycles

Volumn 48, Issue 6, 1998, Pages 1275-1290

  Lounasmaa, Mauri ^a   Berner, Mathias ^a   Tolvanen, Arto ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000020917     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-98-497     Document Type: Article

References (10)

1. J. M. Müller, E. Schlittler, and H. J. Bein, Experientia, 1952, 8, 338.
2. L. Dorfman, A. Furlenmeier, C. F. Huebner, R. Lucas, H. B. MacPhillamy, J. M. Mueller, E. Schlittler, R. Schwyzer, and A. F. St. André, Helv. Chim. Acta, 1954, 37, 59.
3. H. B. MacPhillamy, L. Dorfman, C. F. Huebner, E. Schlittler, and A. F. St. André, J. Am. Chem. Soc., 1955, 77, 1071.
4. E. Schlittler, "Rauwolfia Alkaloids with Special Reference to the Chemistry of Reserpine", in The Alkaloids, Vol. 8, ed. by R. H. F. Manske, Academic Press, New York, 1965, pp. 287-334.
5. See also: T. Kametani and M. Ihara, Heterocycles, 1976, 5, 649.
6. H. B. MacPhillamy, C. F. Huebner, E. Schlittler, A. F. St. André, and P. R. Ulshafer, J. Am. Chem. Soc., 1955, 77, 4335.
7. C. F. Huebner, M. E. Kuehne, B. Korzun, and E. Schiittier, Experientia, 1956, 12, 249.
8. Biogenetic numbering: J. Le Men and W. I. Taylor, Experientia, 1965, 23, 510. The corresponding carbon in indolo[2,3-a]quinolizidines (IUPAC) is C-12b, and in tetrahydro-β-carbolines C-1.
9. R. C. Cookson, Chem. Ind. (London), 1953, 337.
10. M.-M. Janot, R. Goutarel, and M. Amin, C. R. Acad. Sci., 1950, 230, 2041.