Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1649-1658

  Fukazawa, Tetuya ^a   Shimoji, Yasuo ^a   Hashimoto, Toshihiko ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

12 AMINO 2,3,3A,4,11,12,12A,12B OCTAHYDRO 10 HYDROXYISOQUINO[2,1,8 LMA]CARBAZOL 5(1H) ONE; ANTIARRHYTHMIC AGENT; CARBAZOLE DERIVATIVE; CYCLOHEXANOL; TRIACYLGLYCEROL LIPASE;

ARTICLE; DRUG POTENCY; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; HEART ARRHYTHMIA; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 0029934349     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00199-1     Document Type: Article

References (21)

1. a) Shimoji, Y.; Tomita, K.; Hashimoto, T.; Saito, F.; Morisawa, Y.; Mizuno, H.; Yorikane, R.; Koike, H. J. Med. Chem. 1992, 35, 816.
2. b) Shimoji, Y.; Tomita, K.; Karube, T.; Kamioka, T. YAKUGAKU ZASSHI 1992, 112, 804.
3. a) Shimoji, Y.; Saito, F.; Sato, S.; Tomita, K.; Morisawa, Y. Heterocycles 1989, 29, 1871.
4. b) Shimoji, Y.; Saito, F.; Tomita, K.; Morisawa, Y. Heterocycles 1991, 32, 2389.
5. c) Shimoji, Y.; Hashimoto, T.; Furukawa, Y.; Yanagisawa, H. Heterocycles 1993, 36, 123.
6. Asami, M. Chem. Lett. 1984, 829.
7. Kawasaki, M.; Suzuki, Y.; Terashima, S. Chem. Lett. 1984, 239.
8. Sato, T.; Gotoh, Y.; Wakabayashi, Y.; Fujisawa, T. Tetrahedron Lett. 1983, 24, 4123.
9. Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708.
10. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 105, 6237.
11. a) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643.
12. b) Yamasita, H. Chem. Lett. 1987, 525.
13. Fukazawa, T.; Hashimoto, T. Tetrahedron: Asymmetry 1993, 4, 2323.
14. a) Chen, C.-S.; Sih, C. J. Angew. Chem. Int. Ed. Engl. 1989, 28, 695.
15. b) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
16. c) Hiratake, J.; Inagaki, M.; Nishioka, T.; Oda, J. J. Org. Chem. 1988, 53, 6130.
17. d) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
18. a) Corey, E. J.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hammarstrom, S. J. Am. Chem. Soc. 1980, 102, 1436.
19. b) Yamamoto, Y.; Asao, N.; Meguro, M.; Tsukada, N.; Nemoto, H.;Sadayori, N.; Wilson, G.; Nakamura, H. J. Chem. Soc. Chem. Commun. 1993, 1201.
20. c) Bordwell, F. G.; Frame, R. R.; Strong, J. G. J. Org. Chem. 1968, 33, 3385.
21. Yamada, S.; Takamura, N.; Mizoguchi, T. Chem. Prarm. Bull. 1975, 23, 2539.