A facile and efficient asymmetric synthesis of (+)-salsolidine

Tetrahedron Letters

Volumn 41, Issue 29, 2000, Pages 5533-5536

  Taniyama, Daisuke ^a   Hasegawa, Masayoshi ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SALSOLIDINE;

ARTICLE; CYCLIZATION; ENANTIOMER; OXIDATION; PARKINSON DISEASE; PATHOGENESIS; STOICHIOMETRY; SYNTHESIS;

EID: 0034661512     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00830-3     Document Type: Article

References (33)

1. (a) Nagatsu, T. Neurosci. Res. 1997, 29, 99-111.
2. (b) Sano, T. J. Synth. Org. Chem. Jpn. 1999, 57, 136-140.
3. Tetrahydroisoquinoline (TIQ) and 1-methyl TIQ: (a) Yamakawa, T.; Ohta, S. Biochem. Biophys. Res. Commun. 1997, 236, 676-681.
4. (b) Thull, U.; Kneubühler, S.; Gaillard, P.; Carrupt, P.-A.; Testa, B.; Altomare, C.; Carotti, A.; Jenner, P.; McNaught, K. St. P. Biochem. Pharmacol. 1995, 50, 869-877.
5. (c) Kohno, M.; Ohta, S.; Hirobe, M. Biochem. Biophys. Res. Commun. 1986, 140, 448-454. 1-Phenyl TIQ:
6. (d) Gray, N. M.; Cheng, B. K.; Mick, S. J.; Lair, C. M.; Contreras, P. C. J. Med. Chem. 1989, 32, 1242-1248.
7. (e) Charifson, P. S.; Wyrick, S. D.; Hoffman, A. J.; Simmons, R. M. A.; Bowen, J. P.; McDougald, D. L.; Mailman, R. B. J. Med. Chem. 1988, 31, 1941-1946.
8. (a) Maruyama, W.; Naoi, M.; Kasamatsu, T.; Hashizume, Y.; Takahashi, T.; Kohda, K.; Dostert, P. J. Neurochem. 1997, 69, 322-329.
9. (b) Tatton, W. G.; Ju, W. Y. L.; Holland, D. P.; Tai, C.; Kwan, M. J. Neurochem. 1994, 63, 1572-1575.
10. (a) Rozwadowska, M. D. Heterocycles 1994, 39, 903-931.
11. (b) Shinohara, T.; Takeda, A.; Toda, J.; Sano, T. Chem. Pharm. Bull. 1998, 46, 430-433.
12. Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron: Asymmetry 1999, 10, 221-223.
13. Gittins (née Jones), C. A.; North, M. Tetrahedron: Asymmetry 1997, 8, 3789-3799.
14. Enantioselective Pictet-Spengler reaction of β-carboline has been reported. (a) Kawate, T.; Yamada, H.; Soe, T.; Nakagawa, M. Tetrahedron: Asymmetry 1996, 7, 1249-1252.
15. Asymmetric alkylation of an amine: (b) Meyers, A. I. Tetrahedron 1992, 48, 2589-2612.
16. Asymmetric reduction: (c) Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183-187.
17. (d) Willoghby, C. A.; Buchwald, S. L. J. Org. Chem. 1993, 58, 7627-7629.
18. (e) Yamada, K.; Takeda, M.; Iwakuma, T. J. Chem. Soc., Perkin Trans. 1 1983, 265-270.
19. Asymmetric alkylation of an imine: (f) Wünsch, B.; Nerdinger, S. Chem. Lett. 1998, 799-800.
20. (g) Ukaji, Y.; Shimizu, Y.; Kenmoku, Y.; Ahmed, A.; Inomata, K. Chem. Lett. 1997, 59-60.
21. (h) Warrener, R. N.; Liu, L.; Russell, R. A. Chem. Commun. 1997, 2173-2174.
22. (i) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489-8490.
23. For recent asymmetric synthesis of 1, see: (a) Hajipour, A. R.; Hantehzadeh, M. J. Org. Chem. 1999, 64, 8475-8478.
24. (b) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53-56.
25. (c) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7086-7087.
26. (d) Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105-9108.
27. (e) Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709-6712.
28. (f) Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297-310.
29. (g) Murahashi, S.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725-726.
30. (h) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11703-11714.
31. (i) Yamato, M.; Hashigaki, K.; Qais, N.; Ishikawa, S. Tetrahedron 1990, 46, 5909-5920.
32. Karuso, P.; Taylor, W. C. Aust. J. Chem. 1984, 37, 1271-1282.
33. Battersby, A. R.; Edwards, T. P. J. Chem. Soc. 1960, 1214-1221.