New strategy for the synthesis of (±) cherylline dimethyl ether

Asian Journal of Chemistry

Volumn 22, Issue 3, 2010, Pages 1835-1840

  Venugopal, S ^b   Ramanatham, J ^c   Devanna, N ^d   Sanjeev Kumar, A ^a   Ghosh, Samir ^a   Soundararajan, R ^a   Kale, Bhima ^a   Mehta, G N ^a  

^a SARDAR VALLABHBHAI NATIONAL INSTITUTE OF TECHNOLOGY   (India)

^b DR REDDY'S LABORATORIES LTD   (India)

^c ASTRAZENECA   (United Kingdom)

^d JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

Grignard reaction; Pictet spangler cyclization; Reduction; Tetrahydroisoquinolines

Indexed keywords

EID: 77956163523     PISSN: 09707077     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. A. Brossi, G. Grethe, S. Teitel, W.C. Wildman and D.T. Bailey, J. Org. Chem., 35, 1100 (1970).
2. S. Kobayashi, T. Tokumoto and Z. Taira, J. Chem. Soc., Chem. Commun., 1043 (1984).
3. P.S. Charifson, Drugs Fut., 14, 1179 (1989).
4. J. Guillon, P. Dallemagne, H. Leveque, R. Duval and S. Rault, Pharm Sci., 325 (1997).
5. E. Zara-Kaczaim, L. Gyorgy, G. Deak, A. Seregi and M. Doda, J. Med. Chem., 29, 1189 (1986).
6. J. Ulin, A.D. Gee, P. Malmborg, J. Tedroff and B. Laangstroem, Appl. Radiat. Isot., 40, 171 (1989).
7. C. Cherpillod and L.M. Omer, J. Int. Med. Res., 9, 324 (1981).
8. L.M. Omer, Int J. Clin. Pharmacol. Ther. Toxicol., 20, 324 (1982).
9. A. Brossi and S. Teitel, Tetrahedron Lett., 417 (1970).
10. M.A. Schwartz and S.W. Scott, J. Org. Chem., 36, 1827 (1971).
11. T. Kametani, K. Takahashi and C. Van Loc, Tetrahedron, 31, 235 (1975).
12. D.J. Hart, P.A. Cain and D.A. Evans, J. Am. Chem. Soc., 100, 1548 (1978).
13. H. Irie, A. Shiina, T. Fushimi, J. Katakawa, N. Fujii and H. Yajima, Chem. Lett., 875 (1980).
14. S.V. Kessar, P. Singh, R. Chawla and P. Kumar, J. Chem. Soc. Chem. Commun., 1074 (1981).
15. T. Kametani, K. Higashiyama, T. Honda and H. Otomasu, J. Chem. Soc., Perkin Trans I, 2935 (1982).
16. H. Hara, R. Shirai, O. Hoshino and B. Umezawa, Heterocycles, 20, 1945 (1983).
17. H. Hara, R. Shirai, O. Hoshino and B. Umezawa, Chem. Pharm. Bull., 33, 3107 (1985).
18. S. Takano, M. Akiyama and K. Ogasawara, Chem. Lett., 505 (1985).
19. S. Kobayashi, T. Tokumoto, S. Iguchi, M. Kihara, Y. Imakura and Z. Taira, J. Chem. Res. (S), 280 (1986).
20. N.S. Narashimhan and P.A. Patil, J. Chem. Soc. Chem. Commun., 191 (1987).
21. V.G. Gore and N.S. Narashimhan, J. Chem. Soc. Perkin Trans I, 481 (1988).
22. J. Katakawa, H. Yoshimatsu, M. Yoshida, Y. Zhang, H. Irie and H. Yajima, Chem. Pharm. Bull., 36, 3928 (1988).
23. A. Couture, E. Deniau, S. Lebrun and P. Grandclaudon, J. Chem. Soc. Perkin Trans I, 789 (1999).
24. J. Toda, A. Sonobe, T. Ichikawa, T. Saitoh, Y. Horiguchi and T. Sano, Arkivoc, 165 (2000).
25. T. Honda, H. Namiki and F. Satoh, Org. Lett., 3, 631 (2001).
26. A. Couture, E. Deniau, S. Lebrun and P. Grandclaudon, Tetrahedron: Asymm., 14, 1309 (2003).
27. A. Couture, E. Deniau, S. Lebrun and P. Grandclaudon, Org. Biomol. Chem., 1, 1701 (2003).
28. K. Reshma, K. Suvidaha, T. Santosh and K. Janardan, Arkivoc, 256 (2008).