Controlled epimerization of indolo[2,3-a]quinolizidine derivatives: An efficient total synthesis of(±)-tacamonine

Tetrahedron

Volumn 54, Issue 1-2, 1998, Pages 157-164

  Lounasmaa, Mauri ^a   Karinen, Kimmo ^a   Din Belle, David ^a   Tolvanen, Arto ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID; TACAMONINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031986211     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10266-6     Document Type: Article

References (21)

1. 1. Biogenetic numbering: Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508-510. For the numbering of indoloquinolizidines see compound 2.
2. 2. (a) van Beek, T. A.; Lankhorst, P. P.; Verpoorte, R.; Baerheim Svendsen, A. Tetrahedron Lett. 1982, 23, 4827-4830;
3. (b) van Beek, T. A.; Verpoorte, R.; Baerheim Svendsen, A. Tetrahedron 1984, 40, 737-748.
4. 3. Din Belle, D.; Tolvanen, A.; Lounasmaa, M. Tetrahedron 1996, 52, 11361-11378.
5. 4. Lounasmaa, M.; Tolvanen, A. The Eburnamine-Vincamine Alkaloids. In The Alkaloids; Cordell, G. A. Ed.; Academic Press: New York, Vol. 42, 1992; pp. 1-116.
6. 5. Lounasmaa, M.; Karinen, K.; Din Belle, D.; Tolvanen, A. Tetrahedron Lett. 1996, 37, 1513-1516.
7. 6. Tolvanen, A.; Din Belle, D.; Lounasmaa, M. Helv. Chim. Acta 1994, 77, 709-715.
8. 7. All compounds in this work are racemic. For the sake of clarity, some compounds are drawn as their mirror images compared to our earlier work. For example compound 4 (cf. compound 13 in Ref. 3):
9. 8. Lounasmaa, M.; Din Belle, D; Tolvanen, A. Tetrahedron Lett. 1995, 36, 7141-7144.
10. 9. Lounasmaa, M.; Karinen, K.; Din Belle, D.; Tolvanen, A. Heterocycles 1997, 45, 361-366.
11. 10. (a) Oppolzer, W.; Hauth, H.; Pfäffli, P.; Wenger, R. Helv. Chim. Acta 1977, 60, 1801-1810;
12. (b) Sápi, J.; Szabó, L.; Baitz-Gács, E.; Kalaus, G.; Szántay, C.; Karsai-Bihátsi, É. Liebigs Ann. Chem. 1985, 1974-1803.
13. 2: 266.1783, found: 266.1768.
14. 12. Massiot, G.; Sousa Oliveira, F.; Lévy, J. Bull. Soc Chim. Fr. II 1982, 185-190.
15. 13. (a) Ihara, M.; Setsu, F.; Shohda, M.; Taniguchi, N.; Fukumoto, K. Heterocycles 1994, 37, 289-292;
16. (b) Ihara, M.; Setsu, F.; Shohda, M.; Taniguchi, N.; Takunaga, Y.; Fukumoto, K. J. Org. Chem. 1994, 59, 5317-5323.
17. 14. A model study for the synthesis of tacamonine (1) has recently been presented: Clauss, R.; Hunter, R. J. Chem. Soc., Perkin Trans. I 1997, 71-76.
18. 15. (a) Jokela, R.; Schüller, S.; Lounasmaa, M. Heterocycles 1985, 23, 1751-1757.
19. (b) Szabó, L.; Márványos, E.; Tóth, G.; Szántay, Jr., C.; Kalaus, G.; Szántay, C. Heterocycles 1986, 24, 1517-1525.
20. (c) Ihara, M.; Ishida, Y.; Tokunaga, Y.; Kabuto, C.; Fukumoto, K. J. Chem. Soc., Chem. Commun. 1995, 2085-2086.
21. 16. There was a typing error in the reported melting point of (±)-tacamonine in Ref. 3.