Diastereoselective synthesis of 3-oxo-14,15-dihydroandranginine

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6519-6523

  Danieli, B ^a   Lesma, G ^a   Martinelli, M ^a   Passarella, D ^a   Silvani, A ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030863059     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970370e     Document Type: Article

References (29)

1. Kan-Fan, C.; Massiot, G.; Ahond, A.; Das, B. C.; Husson, H.-P.; Potier, P.; Scott, A. I.; Wei, C.-C. J. Chem. Soc., Chem. Commun. 1974, 164.
2. The correct stereochemistry of 1 was elucidated in a second step after the first cis-trans assignment: (a) Massiot, G.; Kan, S. K.; Gonord, P.; Duret, C. J. Am. Chem. Soc. 1975, 97, 3277. (b) Riche, P. C.; Pascard-Billy, C. Acta Crystallogr. 1979, B35, 666.
3. The correct stereochemistry of 1 was elucidated in a second step after the first cis-trans assignment: (a) Massiot, G.; Kan, S. K.; Gonord, P.; Duret, C. J. Am. Chem. Soc. 1975, 97, 3277. (b) Riche, P. C.; Pascard-Billy, C. Acta Crystallogr. 1979, B35, 666.
4. Andriamialisoa, R. Z.; Diatta, L.; Rasoanaivo, P.; Langlois, N.; Potier, P. Tetrahedron 1975, 31, 2347.
5. Saxton reported the total synthesis of 18,19-didehydrotabersonine also as a formal synthesis of andranginine: Blowers, J. W.; Saxton, J. E.; Swanson, A. G. Tetrahedron 1986, 42, 6071.
6. (a) Danieli, B.; Lesma, G.; Palmisano, G.; Passarella, D.; Pyuskyulev, B.; Mai Ngoc, T. J. Org. Chem. 1994, 59, 5810.
7. (b) Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. J. Org. Chem. 1995, 60, 2506. See also refs 8a,b,c.
8. Corey, E. J.; Cheng, X.-M. The Logic of Chemical Synthesis; J. Wiley: New York, 1989.
9. Danieli, B.; Lesma, G.; Luzzani, M.; Passarella, D.; Silvani, A. Tetrahedron 1996, 52, 11291.
10. Benzeneseleninic anhydride (BSA) has been successfully used as selective oxidant for the synthesis and modification of indole alkaloids: (a) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Chem. Commun. 1984, 909. (b) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Perkin Trans. 1 1987, 155. (c) Danieli, B.; Lesma, G.; Palmisano, G.; Passarella, D.; Silvani, A. Tetrahedron 1994, 50, 6941. (d) Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347. (e) Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873.
11. Benzeneseleninic anhydride (BSA) has been successfully used as selective oxidant for the synthesis and modification of indole alkaloids: (a) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Chem. Commun. 1984, 909. (b) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Perkin Trans. 1 1987, 155. (c) Danieli, B.; Lesma, G.; Palmisano, G.; Passarella, D.; Silvani, A. Tetrahedron 1994, 50, 6941. (d) Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347. (e) Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873.
12. Benzeneseleninic anhydride (BSA) has been successfully used as selective oxidant for the synthesis and modification of indole alkaloids: (a) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Chem. Commun. 1984, 909. (b) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Perkin Trans. 1 1987, 155. (c) Danieli, B.; Lesma, G.; Palmisano, G.; Passarella, D.; Silvani, A. Tetrahedron 1994, 50, 6941. (d) Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347. (e) Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873.
13. Benzeneseleninic anhydride (BSA) has been successfully used as selective oxidant for the synthesis and modification of indole alkaloids: (a) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Chem. Commun. 1984, 909. (b) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Perkin Trans. 1 1987, 155. (c) Danieli, B.; Lesma, G.; Palmisano, G.; Passarella, D.; Silvani, A. Tetrahedron 1994, 50, 6941. (d) Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347. (e) Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873.
14. Benzeneseleninic anhydride (BSA) has been successfully used as selective oxidant for the synthesis and modification of indole alkaloids: (a) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Chem. Commun. 1984, 909. (b) Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Perkin Trans. 1 1987, 155. (c) Danieli, B.; Lesma, G.; Palmisano, G.; Passarella, D.; Silvani, A. Tetrahedron 1994, 50, 6941. (d) Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347. (e) Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873.
15. See also Mahbobi, S.; Bernauer, K. Helv. Chim. Acta 1988, 71, 2034.
16. Bigogno, C.; Danieli, B.; Lesma, G.; Passarella, P. Heterocycles 1995, 41, 973.
17. Buchi, G.; Mak, C.-P. J. Org. Chem. 1977, 50, 1784.
18. (a) Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 31, 2647.
19. (b) Parikh, J. R.; Doering, W.von E. J. Am. Chem. Soc. 1967, 89, 5505.
20. Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613.
21. Cook G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575.
22. Energy minimization was performed using the HyperChem program with MM+ force field.
23. Okabe, K.; Natsume, M. Tetrahedron 1991, 47, 7615.
24. Sundberg, R. J.; Amat, M.; Fernando, A. M. J. Org. Chem. 1987, 52, 3151.
25. 1H-COSY confirmed the structure indicated as 35.
26. (a) Li, B.; Smith, M. B. Synth. Commun. 1995, 25, 1265.
27. (b) Ohfume, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511.
28. (a) Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35.
29. (b) Laronze, J. V.; Laronze-Fontane, J.; Levi, J.; Le Men, J. Tetrahedron Lett. 1974, 15, 491.