Short synthesis of (±)-hirsutine: Direct addition of dimethyl malonate anion to a 1,4-conjugate iminium salt of appropriate 3-ethylindolo[2,3-a]quinolizidine

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1455-1458

  Lounasmaa, Mauri ^a   Miettinen, Jari ^a   Hanhinen, Pirjo ^a   Jokela, Reija ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

HIRSUTINE; INDOLE ALKALOID;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031584885     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00056-7     Document Type: Article

References (18)

1. 1. Grierson, D. S.; Harris, M.; Husson, H.-P.; J. Am. Chem. Soc. 1980, 102, 1064-1082.
2. 2. Husson, H.-P.; Bull. Soc. Chim. Belg. 1982, 91, 985-995.
3. 3. Koskinen, A.; Lounasmaa, M.; J. Chem. Soc., Chem. Commun. 1983, 821-822.
4. 4. Koskinen, A.; Lounasmaa, M.; Tetrahedron Lett. 1983, 24, 1951-1952. See also, Lounasmaa, M.; Synthetic Studies in the Field of Indole Alkaloids, in "Studies in Natural Products Chemistry", (Atta-ur-Rahman, Ed.), Vol. 1, Elsevier, Amsterdam, 1988, pp. 89-122.
5. 4. Koskinen, A.; Lounasmaa, M.; Tetrahedron Lett. 1983, 24, 1951-1952. See also, Lounasmaa, M.; Synthetic Studies in the Field of Indole Alkaloids, in "Studies in Natural Products Chemistry", (Atta-ur-Rahman, Ed.), Vol. 1, Elsevier, Amsterdam, 1988, pp. 89-122.
6. 5. Grierson, D. S.; Vuilhorgne, M.; Husson, H.-P.; Lemoine, G.; J. Org. Chem. 1982, 47, 4439-4452.
7. 6. Grierson, D. S.; Harris, M.; Husson, H.-P.; Tetrahedron 1983, 39, 3683-3694.
8. 7. Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M.; Tetrahedron 1989, 45, 2683-2692. See also, Lounasmaa, M.; Synthetic Studies in the Field of Indole Alkaloids. Part 2, in "Studies in Natural Products Chemistry" (Atta-ur-Rahman, Ed.), Vol. 14, Elsevier, Amsterdam, 1994, pp. 703-730.
9. 7. Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M.; Tetrahedron 1989, 45, 2683-2692. See also, Lounasmaa, M.; Synthetic Studies in the Field of Indole Alkaloids. Part 2, in "Studies in Natural Products Chemistry" (Atta-ur-Rahman, Ed.), Vol. 14, Elsevier, Amsterdam, 1994, pp. 703-730.
10. 7
11. 4: 382.1893.
12. 4: 384.2049.
13. 11. Wenkert, E.; Vankar, Y. D.; Yadav, J. S.; J. Am. Chem. Soc. 1980, 102, 7971-7972.
14. 12. Brown, R. T.; Jones, M. F.; Wingfield, M.; J. Chem. Soc., Chem. Commun. 1984, 847-848.
15. 13. Gomez-Pardo, D.; Desmaële, D.; d'Angelo, J.; Tetrahedron Lett. 1992, 33, 6633-6636.
16. 14. Lounasmaa, M.; Johansson, C.-J.; Tetrahedron 1977, 33, 113-117.
17. 15. Lounasmaa, M.; Jokela, R.; Tirkkonen, B.; Miettinen, J.; Halonen, M.; Heterocycles 1992, 34, 321-339.
18. 16. Lounasmaa, M.; Jokela, R.; Bäck, M.; Hanhinen, P.; Laine, C.; Tetrahedron 1995, 51, 11891-11900.