Novel reduction of 3-hydroxypyridine and its use in the enantioselective synthesis of (+)-pseudoconhydrine and (+)-N-methylpseudoconhydrine

Chemical Communications

Volumn , Issue 12, 1996, Pages 1433-1434

  Sakagami, Hideki ^a   Kamikubo, Takashi ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002244258     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001433     Document Type: Article

References (13)

1. F. W. Fowler, J. Org. Chem., 1972, 37, 1321.
2. R. J. Sundberg, G. Hamilton and C. Trindle, J. Org. Chem., 1986, 51, 3672.
3. Pertinent reviews, see: G. M. Strunz and J. A. Findley, The Alkaloids, 1985, 26, 89; O. Plunkett, Nat. Prod. Rep., 1994, 11, 581 and previous reports.
4. Pertinent reviews, see: G. M. Strunz and J. A. Findley, The Alkaloids, 1985, 26, 89; O. Plunkett, Nat. Prod. Rep., 1994, 11, 581 and previous reports.
5. Previous chiral syntheses of pseudoconhydrine, see: (a) K. Tadano, Y. Iimura and T. Suami, J. Carbohyd. Chem., 1985, 4, 129; (b) H. Takahata, K. Inoue and T. Momose, Heterocycles, 1994, 38, 269.
6. Previous chiral syntheses of pseudoconhydrine, see: (a) K. Tadano, Y. Iimura and T. Suami, J. Carbohyd. Chem., 1985, 4, 129; (b) H. Takahata, K. Inoue and T. Momose, Heterocycles, 1994, 38, 269.
7. Previous chiral syntheses of N-methylpseudoconhydrine, see: (a) T. Shono, Y. Matsumura, O. Onomura and M. Sato, J. Org. Chem., 1988, 53, 4118; (b) ref 4b; (c) C. Herdeis, W. A. Held, A. Kirfel and F. Schwabenländer, Liebigs Ann. Chem., 1995, 1295.
8. Previous chiral syntheses of N-methylpseudoconhydrine, see: (a) T. Shono, Y. Matsumura, O. Onomura and M. Sato, J. Org. Chem., 1988, 53, 4118; (b) ref 4b; (c) C. Herdeis, W. A. Held, A. Kirfel and F. Schwabenländer, Liebigs Ann. Chem., 1995, 1295.
9. Previous chiral syntheses of N-methylpseudoconhydrine, see: (a) T. Shono, Y. Matsumura, O. Onomura and M. Sato, J. Org. Chem., 1988, 53, 4118; (b) ref 4b; (c) C. Herdeis, W. A. Held, A. Kirfel and F. Schwabenländer, Liebigs Ann. Chem., 1995, 1295.
10. A pertinent monograph, see: C.-H. Wong and G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Pergamon Press, Oxford, 1994.
11. Cf. P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983.
12. Cf. H. Sakagami, K. Samizu, T. Kamikubo and K. Ogasawara, Synlett, 1996, 163.
13. L. Marion and W. F. Cockburn, J. Am. Chem. Soc., 1949, 71, 3402.