First enantiocontrolled syntheses of (+)-uleine and (+)-dasycarpidone

Chemical Communications

Volumn , Issue 8, 1997, Pages 765-766

  Saito, Masanori ^a   Kawamura, Mitsuhiro ^a   Hiroya, Kou ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOID;

ARTICLE; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030969288     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700856b     Document Type: Article

References (27)

1. J. E. Saxton, Nat. Prod. Rep., 1995, 12, 385 and the former reports; The Chemistry of Heterocyclic Compounds, ed. J. E. Saxton, Wiley-Interscience, New York, 1983, vol. 25, part 4, ch. 4; supplement to part 4, 1994.
2. J. E. Saxton, Nat. Prod. Rep., 1995, 12, 385 and the former reports; The Chemistry of Heterocyclic Compounds, ed. J. E. Saxton, Wiley-Interscience, New York, 1983, vol. 25, part 4, ch. 4; supplement to part 4, 1994.
3. J. E. Saxton, Nat. Prod. Rep., 1995, 12, 385 and the former reports; The Chemistry of Heterocyclic Compounds, ed. J. E. Saxton, Wiley-Interscience, New York, 1983, vol. 25, part 4, ch. 4; supplement to part 4, 1994.
4. Racemic syntheses: (a) A. Jackson, N. D. V. Wilson, A. J. Gaskell and J. A. Joule, J. Chem. Soc. C, 1969, 2738; (b) L. J. Dolby and H. Biere, J. Org. Chem., 1970, 35, 3843; (c) T. Kametani and T. Suzuki, J. Org. Chem., 1971, 36, 1291; (d) J. Gracia, N. Casamitjana, J. Bonjoch and J. Bosch, J. Org. Chem., 1994, 59, 3939; (e) G. Büchi, S. J. Gould and F. Näf, J. Am. Chem. Soc., 1971, 93, 2492.
5. Racemic syntheses: (a) A. Jackson, N. D. V. Wilson, A. J. Gaskell and J. A. Joule, J. Chem. Soc. C, 1969, 2738; (b) L. J. Dolby and H. Biere, J. Org. Chem., 1970, 35, 3843; (c) T. Kametani and T. Suzuki, J. Org. Chem., 1971, 36, 1291; (d) J. Gracia, N. Casamitjana, J. Bonjoch and J. Bosch, J. Org. Chem., 1994, 59, 3939; (e) G. Büchi, S. J. Gould and F. Näf, J. Am. Chem. Soc., 1971, 93, 2492.
6. Racemic syntheses: (a) A. Jackson, N. D. V. Wilson, A. J. Gaskell and J. A. Joule, J. Chem. Soc. C, 1969, 2738; (b) L. J. Dolby and H. Biere, J. Org. Chem., 1970, 35, 3843; (c) T. Kametani and T. Suzuki, J. Org. Chem., 1971, 36, 1291; (d) J. Gracia, N. Casamitjana, J. Bonjoch and J. Bosch, J. Org. Chem., 1994, 59, 3939; (e) G. Büchi, S. J. Gould and F. Näf, J. Am. Chem. Soc., 1971, 93, 2492.
7. Racemic syntheses: (a) A. Jackson, N. D. V. Wilson, A. J. Gaskell and J. A. Joule, J. Chem. Soc. C, 1969, 2738; (b) L. J. Dolby and H. Biere, J. Org. Chem., 1970, 35, 3843; (c) T. Kametani and T. Suzuki, J. Org. Chem., 1971, 36, 1291; (d) J. Gracia, N. Casamitjana, J. Bonjoch and J. Bosch, J. Org. Chem., 1994, 59, 3939; (e) G. Büchi, S. J. Gould and F. Näf, J. Am. Chem. Soc., 1971, 93, 2492.
8. Racemic syntheses: (a) A. Jackson, N. D. V. Wilson, A. J. Gaskell and J. A. Joule, J. Chem. Soc. C, 1969, 2738; (b) L. J. Dolby and H. Biere, J. Org. Chem., 1970, 35, 3843; (c) T. Kametani and T. Suzuki, J. Org. Chem., 1971, 36, 1291; (d) J. Gracia, N. Casamitjana, J. Bonjoch and J. Bosch, J. Org. Chem., 1994, 59, 3939; (e) G. Büchi, S. J. Gould and F. Näf, J. Am. Chem. Soc., 1971, 93, 2492.
9. Utilization of (+)-norcamphor as a starting material for enantiocontrolled syntheses of natural products: (a) M. Kawamura and K, Ogasawara, Tetrahedron Lett., 1995, 36, 3369; (b) M. Saito, M. Kawamura and K. Ogasawara, Tetrahedron Lett., 1995, 36, 9003; (c) M. Kawamura and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1995, 2403; (d) M. Kawamura and K. Ogasawara, Heterocycles, 1997, 44, 129.
10. Utilization of (+)-norcamphor as a starting material for enantiocontrolled syntheses of natural products: (a) M. Kawamura and K, Ogasawara, Tetrahedron Lett., 1995, 36, 3369; (b) M. Saito, M. Kawamura and K. Ogasawara, Tetrahedron Lett., 1995, 36, 9003; (c) M. Kawamura and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1995, 2403; (d) M. Kawamura and K. Ogasawara, Heterocycles, 1997, 44, 129.
11. Utilization of (+)-norcamphor as a starting material for enantiocontrolled syntheses of natural products: (a) M. Kawamura and K, Ogasawara, Tetrahedron Lett., 1995, 36, 3369; (b) M. Saito, M. Kawamura and K. Ogasawara, Tetrahedron Lett., 1995, 36, 9003; (c) M. Kawamura and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1995, 2403; (d) M. Kawamura and K. Ogasawara, Heterocycles, 1997, 44, 129.
12. Utilization of (+)-norcamphor as a starting material for enantiocontrolled syntheses of natural products: (a) M. Kawamura and K, Ogasawara, Tetrahedron Lett., 1995, 36, 3369; (b) M. Saito, M. Kawamura and K. Ogasawara, Tetrahedron Lett., 1995, 36, 9003; (c) M. Kawamura and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1995, 2403; (d) M. Kawamura and K. Ogasawara, Heterocycles, 1997, 44, 129.
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21. Utilization of this procedure for the natural product synthesis: S. Takano, T. Sato, K. Inomata and K. Ogasawara, J. Chem. Soc, Chem. Commun., 1991, 402; K. Shin and K. Ogasawara, Chem. Lett., 1995, 289; K. Shin and K. Ogasawara, Synlett, 1995, 859; K. Shin and K. Ogasawara, Synlett, 1996, 922.
22. Utilization of this procedure for the natural product synthesis: S. Takano, T. Sato, K. Inomata and K. Ogasawara, J. Chem. Soc, Chem. Commun., 1991, 402; K. Shin and K. Ogasawara, Chem. Lett., 1995, 289; K. Shin and K. Ogasawara, Synlett, 1995, 859; K. Shin and K. Ogasawara, Synlett, 1996, 922.
23. Utilization of this procedure for the natural product synthesis: S. Takano, T. Sato, K. Inomata and K. Ogasawara, J. Chem. Soc, Chem. Commun., 1991, 402; K. Shin and K. Ogasawara, Chem. Lett., 1995, 289; K. Shin and K. Ogasawara, Synlett, 1995, 859; K. Shin and K. Ogasawara, Synlett, 1996, 922.
24. K. Sonogashira, Y. Tohda and N. Hagiwara, Tetrahedron Lett., 1975, 4467.
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