Vinyl imidates in cycloaddition reactions: A formal synthesis of (±)-reserpine

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2265-2267

  Sparks, Steven M ^a   Shea, Kenneth J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDOESTER; ISOQUINOLINE DERIVATIVE; RESERPINE; VINYL DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

IMIDOESTERS; ISOQUINOLINES; RESERPINE; VINYL COMPOUNDS;

EID: 0035954873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015988w     Document Type: Article

References (17)

1. Woodson, R. E.; Youngken, H. W.; Schittler, E.; Schneider, J. A. Rauwolfia: Botany, Pharmacognosy, Chemistry and Pharmacology; Little, Brown and Co.: Boston, 1957.
2. For recent reviews, see: (a) Baxter, E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer-Verlag: New York, 1992; Vol 8, pp 197-319.
3. (b) Szántay, C.; Honty, K. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley & Sons: Chinchester, 1994; Chapter 4, pp 161-216.
4. Hanessian, S.; Pan, J.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem. 1997, 62, 465.
5. (a) Shea, K. J.; Svoboda, J. J. Tetrahedron Lett. 1986, 27, 4837.
6. (b) Gutierrez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989, 54, 4335.
7. Sparks, S. M.; Shea, K. J. Tetrahedron Lett. 2000, 41, 6721.
8. (a) Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157.
9. (b) Wender, P. A.; Schaus, J. M.; White, A. W. Heterocycles 1987, 25, 263.
10. Farina, V.; Krishnamurthy, A.; Scott, W. J. Org. React. 1997, 50, 1.
11. Paterson, I.; Febner, K.; Finlay, M. R. V.; Jacobs, M. F. Tetrahedron Lett. 1996, 37, 8803.
12. Weir, J. R.; Patel, B. A.; Heck, R. F. J. Org. Chem. 1980, 45, 4926.
13. Greico, P. A.; Yoshida, K.; He, A. Tetrahedron Lett. 1984, 25, 5715.
14. Bald, E.; Saigo, Z.; Mukaiyama, T. Chem. Lett. 1975, 1163.
15. Under the coupling conditions, a minor amount (>5%) of cycloadduct was observed. The origin of cycloadduct may result from an intermediate N-acyliminium ion produced from the coupling reaction. This raises the possibility of protonic or Lewis acid catalysis of the cycloaddition step. This chemistry is currently being pursued.
16. Cycloaddition in refluxing benzene provided a lower endolexo ratio (4:1).
17. Baxter, E. W.; Labaree, D.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 7682.