Biomimetic construction of the tetracyclic ring system of ngouniensine

Tetrahedron

Volumn 55, Issue 52, 1999, Pages 14995-15000

  Passarella, Daniele ^a   Martinelli, Marisa ^a   Llor, Núria ^b   Amat, Mercedes ^b   Bosch, Joan ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Alkaloids; Biomimetic reactions; Indoles

Indexed keywords

INDOLE ALKALOID; NGOUNIENSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

STRYCHNOS;

EID: 0033601419     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00956-4     Document Type: Article

References (26)

1. a) Indole and Biogenetically Related Alkaloids, Phillipson, J. D. and Zenk, M. H., Eds.; Academic Press, London, 1980.
2. b) For recent achievements in the indole alkaloid field, see: Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1997, 62, 3597-3609.
3. Scott, A. I.; Yeh, C. L. J. Am. Chem. Soc. 1974, 96, 2273-2274.
4. A similar mechanism could explain the formation in nature of Strychnos alkaloids both in racemic form (pseudoakuammicine, scholarine, vinervidine) and possessing an absolute configuration at C-15 opposite to that of (-)-secologanine . For a review, see: Bosch, J.; Bonjoch, J.; Amat, M. in The Alkaloids, Cordell, G. A., Ed.; Vol. 48, pp 75-189; Academic Press, Inc., New York, 1996.
5. a) Massiot, G.; Zèches, M.; Thépenier, P.; Jacquier, M.-J.; Le Men-Olivier, L.; Delaude, C. J. Chem. Soc., Chem. Commun. 1982, 768-769.
6. b) Massiot, G.; Thépenier, P.; Jacquier, M.-J.; Lounkokobi, J.; Mirand, C.; Zèches, M.; Le Men-Olivier, L.; Delaude, C. Tetrahedron 1983, 39, 3645-3656.
7. a) Kuehne, M. E.; Frasier, D. A.; Spitzer, T. D. J. Org. Chem. 1991, 56, 2696-2700.
8. b) Kuehne, M. E.; Brook, C. S.; Frasier, D. A.; Xu, F. J. Org. Chem. 1994, 59, 5977-5982.
9. a) DiNinno, F.; Heckle, W. L.; Rehse, D. K.; Wilson, R. M. Tetrahedron Lett. 1972, 2639-2642.
10. b) Wilson, R. M.; Farr, R. A.; Burlett, D. J. J. Org. Chem. 1981, 46, 3293-3302.
11. a) Bosch, J.; Bennasar, M.-L.; Zulaica, E.; Massiot, G.; Massoussa, B. Tetrahedron Lett. 1987, 28, 231-234.
12. b) Bennasar, M.-L.; Zulaica, E.; Bosch, J. Heterocycles 1989, 29, 381-390.
13. a) Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299-6312.
14. b) Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 59, 3939-3951.
15. c) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158-3175.
16. d) Amat, M.; Coll, M.-D.; Bosch, J.; Espinosa, E.; Molins, E. Tetrahedron Asymmetry 1997, 8, 935-948.
17. e) Bonjoch, J.; Solé, D.; García-Rubio, S.; Bosch, J. J. Am. Chem. Soc. 1997, 119, 7230-7240.
18. f) Solé, D.; Bonjoch, J.; García-Rubio, S.; Peidró, E.; Bosch, J. Angew. Chem., Int. Ed. Engl. 1999, 38, 395-397.
19. 2-Cyanotetrahydropyridines are latent forms of dihydropyridinium cations: Grierson, D. S.; Harris, M.; Husson, H.-P. J. Am. Chem. Soc. 1980, 102, 1064-1082.
20. a) Wenkert, E.; Massy-Westropp, R. A.; Lewis, R. G. J. Am. Chem. Soc. 1962, 84, 3732-3736.
21. b) Grierson, D. S.; Vuilhorgne, M.; Husson, H.-P.; J. Org. Chem. 1982, 47, 4439-4452.
22. Parsons, R. L.; Berk, J. D.; Kuehne, M. E. J. Org. Chem. 1993, 58, 7482-7489.
23. Kuehne, M. E.; Xu, F. J. Org. Chem. 1997, 62, 7950-7960.
24. For a review, see: Grierson, D. S. Org. React. 1991, 39, 85-295.
25. 3) δ 9.60 (1H, d, J = 6.5 Hz), 9.01 (1H, s), 7.95 (1H, d, J = 8.0 Hz), 7.83 (1H, d, J = 8.0 Hz), 7.61 (1H, t, J = 6.5 Hz), 7.12 (1H, t, J = 8.0 Hz), 6.90 (1H, t, J = 8.0 Hz), 6.83 (1H, d, J = 6.5 Hz), 5.22 (2H, t, J = 5.0 Hz), 4.21 (2H, q, , J = 7.0 Hz), 4.05 (2H, s), 3.55 (2H, t, J = 7.0 Hz), 2.55 (2H, q, J = 7.0 Hz), 1.63 (9H, s), 1.32 (3H, t, J = 7.0 Hz), 0.92 (3H, t, J = 7.0 Hz).
26. For a similar result, see: Passarella, D.; Sathyanarayana, S.; Amat, M.; Bosch, J. Nat. Prod. Lett. 1996, 8, 75-82.