Chiral synthesis of phosphodiesterase inhibitor, (R)-(-)-rolipram, by means of enantioselective deprotonation strategy

Heterocycles

Volumn 42, Issue 1, 1996, Pages 109-112

  Honda, Toshio ^a   Ishikawa, Fumihiro ^a   Kanai, Kazuo ^a   Sato, Shigeki ^b   Kato, Daishiro ^b   Tominaga, Hideo ^b  

^a HOSHI UNIVERSITY   (Japan)

^b JPS Pharmaceutical Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000637512     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S33     Document Type: Article

References (20)

1. T. Honda, N. Kimura, and M. Tsubuki, Tetrahedron: Asymmetry, 1993, 4, 1475
2. a) K. Koga, Yuki Gosei Kagaku Kyokaishi, 1990, 48, 463;
3. b) N. S. Simpkins, Chem. Soc. Rev., 1990, 19, 335;
4. c) P. J. Cox and N. S. Simpkins, Tetrahedron: Asymmetry, 1991, 2, 1 and references cited therein.
5. a) T. Honda and N. Kimura, J. Chem. Soc., Chem. Commun., 1994, 77;
6. b) T. Honda, N. Kimura, S. Sato, D. Kato, and H. Tominaga, J. Chem. Soc., Perkin Trans. 1, 1994, 1043.
7. C. W. Davis, Biochem. Biophys. Acta, 1984, 797, 354.
8. U. Schwabe, M. Miyake, Y. Ohgi, and J. W. Daly, Mol. Pharmacol., 1976, 12, 900.
9. G. Nemoz, M. Moueqqit, A. -F. Prigent, and H. Pacheco, Eur. J. Biochem., 1989, 184, 511.
10. M. L. Reeves, B. K. Leigh, and P. J. England, Biochem. J., 1987, 241, 535.
11. J. A. Beavo and D. H. Reifsnyder, Trends Pharm. Sci., 1990, 11, 150.
12. a) H. Wachtel, J. Pharm. Pharmacol., 1983, 35, 440;
13. b) R. Schmiechen, H. H. Schneider, and H. Wachtel, Psychopharmacology, 1990, 102, 117.
14. The synthesis of (R)-(-)-rolipram: a) J. Mulzer, R. Zuhse, and R. Schmiechen, Angew. Chem., Int. Ed. Engl., 1992, 31, 870; b) P. W. Baures, D. S. Eggleston, K. F. Erhard, L. B. Cieslinski, T. J. Torphy, and S. B. Christensen, J. Med. Chem., 1993, 36, 3274; c) A. I. Meyers and L. Snyder, J. Org. Chem., 1993, 58, 36 and references cited therein.
15. The synthesis of (R)-(-)-rolipram: a) J. Mulzer, R. Zuhse, and R. Schmiechen, Angew. Chem., Int. Ed. Engl., 1992, 31, 870; b) P. W. Baures, D. S. Eggleston, K. F. Erhard, L. B. Cieslinski, T. J. Torphy, and S. B. Christensen, J. Med. Chem., 1993, 36, 3274; c) A. I. Meyers and L. Snyder, J. Org. Chem., 1993, 58, 36 and references cited therein.
16. The synthesis of (R)-(-)-rolipram: a) J. Mulzer, R. Zuhse, and R. Schmiechen, Angew. Chem., Int. Ed. Engl., 1992, 31, 870; b) P. W. Baures, D. S. Eggleston, K. F. Erhard, L. B. Cieslinski, T. J. Torphy, and S. B. Christensen, J. Med. Chem., 1993, 36, 3274; c) A. I. Meyers and L. Snyder, J. Org. Chem., 1993, 58, 36 and references cited therein.
17. A. E. Greene, J. -P. Lansard, J. -L. Luche, and C. Petrier, J. Org. Chem., 1983, 48, 4763.
18. C. M. Cain, R. P. C. Cousins, G. Coumbarides, and N. S. Simpkins, Tetrahedron, 1990, 46, 523.
19. B. Lal, B. N. Praraanik, M. S. Manhas, and A. K. Bose, Tetrahedron Lett., 1977, 1977.
20. S. N. Maiti, P. Spevak, and A. V. N. Reddy, Synth. Commun., 1988, 18, 1201.