General Approach to the Synthesis of Sarpagine and Ajmaline Alkaloids. Enantiospecific Total Synthesis of (+)-Ajmaline and Alkaloid G via the Asymmetric Pictet-Spengler Reaction

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4166-4167

  Li, Jin ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000656873     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980476p     Document Type: Article

References (17)

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3. Hamaker, L. K.; Cook, J. M. The Synthesis of Macroline-Related Alkaloids. In Alkaloids: Chemical and Biological Perspectives', Pelletier, S. W., Ed.; Pergamon Press: London, 1995; pp 23-84 and references cited therein.
4. Endreb, S.; Takayama, H.; Suda, S.; Kitajima, M.; Aimi, N.; Sakai, S.; Stöckigt, J. Phytochemistry 1993, 32, 725-730.
5. For earlier syntheses of ajmaline see: (a) Masamune, S.; Ang, S. K.; Egli, C.; Nakatsuka, N.; Sarkar, S. K; Yasunari, Y. J. Am. Chem. Soc. 1967, 89, 2506-2507. (b) Van Tamelen, E. E.; Oliver, L. K. Bioorg. Chem. 1976, 5 309-326. (c) Mashimo, K; Sato, Y. Tetrahedron Lett. 1969, 11, 905-906. For a synthesis of isoajmaline see: Mashimo, K.; Sato, Y. Tetrahedron Lett. 1969, 11, 901-904.
6. For earlier syntheses of ajmaline see: (a) Masamune, S.; Ang, S. K.; Egli, C.; Nakatsuka, N.; Sarkar, S. K; Yasunari, Y. J. Am. Chem. Soc. 1967, 89, 2506-2507. (b) Van Tamelen, E. E.; Oliver, L. K. Bioorg. Chem. 1976, 5 309-326. (c) Mashimo, K; Sato, Y. Tetrahedron Lett. 1969, 11, 905-906. For a synthesis of isoajmaline see: Mashimo, K.; Sato, Y. Tetrahedron Lett. 1969, 11, 901-904.
7. For earlier syntheses of ajmaline see: (a) Masamune, S.; Ang, S. K.; Egli, C.; Nakatsuka, N.; Sarkar, S. K; Yasunari, Y. J. Am. Chem. Soc. 1967, 89, 2506-2507. (b) Van Tamelen, E. E.; Oliver, L. K. Bioorg. Chem. 1976, 5 309-326. (c) Mashimo, K; Sato, Y. Tetrahedron Lett. 1969, 11, 905-906. For a synthesis of isoajmaline see: Mashimo, K.; Sato, Y. Tetrahedron Lett. 1969, 11, 901-904.
8. For earlier syntheses of ajmaline see: (a) Masamune, S.; Ang, S. K.; Egli, C.; Nakatsuka, N.; Sarkar, S. K; Yasunari, Y. J. Am. Chem. Soc. 1967, 89, 2506-2507. (b) Van Tamelen, E. E.; Oliver, L. K. Bioorg. Chem. 1976, 5 309-326. (c) Mashimo, K; Sato, Y. Tetrahedron Lett. 1969, 11, 905-906. For a synthesis of isoajmaline see: Mashimo, K.; Sato, Y. Tetrahedron Lett. 1969, 11, 901-904.
9. Hobson, J. D.; McCluskey, J. G. J. Chem. Soc. C 1967, 20, 2015-2017.
10. Cox, E. D.; Hamaker, L. K.; Li, Jin; Yu, Peng; Czerwinski, K. M.; Li, Deng; Cook, J. M. J. Org. Chem. 1997, 62, 44-61. Yu, Peng; Cook, J. M. Tetrahedron Lett. 1997, 38, 6819-6822 and references cited therein.
11. Cox, E. D.; Hamaker, L. K.; Li, Jin; Yu, Peng; Czerwinski, K. M.; Li, Deng; Cook, J. M. J. Org. Chem. 1997, 62, 44-61. Yu, Peng; Cook, J. M. Tetrahedron Lett. 1997, 38, 6819-6822 and references cited therein.
12. Fu, X.; Cook, J. M. J. Org. Chem. 1993, 58, 661-672.
13. 20 = +144).
14. 2, TFA (80% yield)].
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