Alkaloid synthesis using chiral δ-amino β-ketoesters: A stereoselective synthesis of (-)-lasubine II

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2623-2625

  Davis, Franklin A ^a   Chao, Bin ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMINO ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LASUBIN I; QUINOLIZINE DERIVATIVE;

ARTICLE; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AMINO ACIDS; INDICATORS AND REAGENTS; QUINOLIZINES; STEREOISOMERISM;

EID: 0034710496     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061438     Document Type: Article

References (20)

1. (a) Golebiewski, W. M.; Wrobel, J. T. In The Alkaloids; Academic Press: New York, 1981; Vol. 18, Chapter 4, p 263.
2. (b) Fuji, K. In The Alkaloids; Academic Press: New York, 1989; Vol. 35, Chapter 3, p 155.
3. Michael, J. P. Nat. Prod. Rep. 1997, 14, 21.
4. Fuji, K.; Yamada, T.; Fujita, E.; Murata, H. Chem. Pharm. Bull. 1978, 26, 2515.
5. For references to the synthesis of racemic lasubine alkaloids, see: Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C. Tetrahedron: Asymmetry 1998, 9, 4361.
6. Comins, D. L.; LaMunyon, D. H. J. Org. Chem. 1992, 57, 5807.
7. Ratni, H.; Kündig, E. P. Org. Lett. 1999, 1, 1997.
8. Ukaji, Y.; Ima, M.; Yamada, T.; Inomata, K. Heterocycles 2000, 52, 563.
9. Davis, F. A.; Chao, B.; Fang, T.; Szewczyk, J. M. Org. Lett. 2000, 2, 1041.
10. (a) Davis, F. A.; Zhang, Y. Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
11. (b) Fanelli, D. L.; Szewczyk, J. M.; Zhang, Y.; Reddy, G. V.; Burns, D. M.; Davis, F. A. Org. Synth. 1999, 77, 50.
12. Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chim. Acta 1986, 69, 803.
13. Hua, D. H.; Miao, S. W.; Bharathi, S. N.; Katsuhira, T.; Bravo, A. A. J. Org. Chem. 1990, 55, 3682.
14. Tamao, K.; Kodama, S.; Nakajima, I.; Kumada, M.; Minato, A.; Suzuki, K. Tetrahedron 1982, 38, 3347.
15. Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656.
16. Rubottom, G. M.; Kim, C.-w. J. Org. Chem. 1983, 48, 1550.
17. For a review on the reation of carboxylic acids with organolithium reagents, see: Jorgenson, M. J. Org. React. 1970, 18, 1.
18. Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1978, 43, 1064.
19. For a review on Weinreb amides see: Sibi, M. P. Org. Prep. Proc. Int. 1993, 25, 15.
20. Davis, F. A.; Kasu, P. V. N. Tetrahedron Lett. 1998, 39, 6135.