Short synthetic route to (±)-geissoschizine

Tetrahedron

Volumn 52, Issue 19, 1996, Pages 6803-6810

  Lounasmaa, Mauri ^a   Jokela, Reija ^a   Anttila, Ulla ^a   Hanhinen, Pirjo ^a   Laine, Christiane ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

GEISSOSCHIZINE; INDOLE ALKALOID;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029932476     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00292-X     Document Type: Article

References (22)

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3. Allorge, L. , Mémoires du Muséum National d'Histoire Naturelle, Nouvelle Série, Sér. B, Botanique, 1985, 30, 114.
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5. Lounasmaa, M.; Tolvanen, A., in "The Monoterpenoid Indole Alkaloids" (Saxton, J. E., Ed.), 2nd Ed., Wiley, London, 1994, pp. 57-159, and references cited therein.
6. Rapoport, H.; Windgassen, R.J.; Hughes, N.A.; Onak, T.P., J. Am. Chem. Soc. 1959, 81, 3166-3167. Idem, Ibid. 1960, 82, 4404-4414.
7. Rapoport, H.; Windgassen, R.J.; Hughes, N.A.; Onak, T.P., J. Am. Chem. Soc. 1959, 81, 3166-3167. Idem, Ibid. 1960, 82, 4404-4414.
8. Janot, M.-M., Tetrahedron 1961, 14, 113-125.
9. Le Men, J.; Taylor, W.I., Experientia 1965, 21, 508-510.
10. Szántay, Cs.; Blaskó, G.; Honty, K.; Dörnyei, G., in "The Alkaloids" (Brossi, A., Ed.), Vol. 27., Academic Press, London, 1986, pp. 131-268, and references cited therein.
11. Brown, R. T., in "The Monoterpenoid Indole Alkaloids" (Saxton, J. E., Ed.), Wiley, New York, 1983, pp. 63-146 and references cited therein.
12. Tirkkonen, B.; Miettinen, J.; Salo, J.; Jokela, R.; Lounasmaa, M., Tetrahedron 1994, 50, 3537-3556. The earlier indicated total yield of 32% and ratio 5/4 between compounds 2 and 3 were changed into 50% and 6/1 by even more careful elimination of the moisture.
13. Lounasmaa, M.; Tamminen, T., Tetrahedron 1991, 47, 2879-2894. See also, Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M., Tetrahedron 1989, 45, 2683-2692.
14. Lounasmaa, M.; Tamminen, T., Tetrahedron 1991, 47, 2879-2894. See also, Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M., Tetrahedron 1989, 45, 2683-2692.
15. Potier, P., Rev. Latinoamer. Quím. 1978, 9, 47-54. See also, Lounasmaa, M.; Koskinen, A., Heterocycles 1984, 22, 1591-1612.
16. Potier, P., Rev. Latinoamer. Quím. 1978, 9, 47-54. See also, Lounasmaa, M.; Koskinen, A., Heterocycles 1984, 22, 1591-1612.
17. a-Boc group were detected in some reaction products (carefully purified starting materials). This indicates that, under the reaction conditions used, the Boc-group migrates in some degree from oxygen to nitrogen.
18. Takayama, H.; Watanabe, T.; Seki, H.; Aimi, N.; Sakai, S.; Tetrahedron Lett. 1992, 33, 6831-6834.
19. 15 is not possible in compound 8.
20. Yamada, K.; Aoki, K.; Kato, T.; Uemura, D.; van Tamelen, E. E., J. Chem. Soc., Chem. Comm. 1974, 908-909.
21. Wenkert, E.; Vankar, Y. D.; Yadav, J. S., J. Am. Chem. Soc. 1980, 102, 7971-7972.
22. Overman, L. E.; Robichaud, A. J., J. Am. Chem. Soc. 1989, 111, 300-308.