Enantioselective total synthesis of (+)-amabiline

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1869-1871

  Senter, Timothy J ^a   Fadeyi, Olugbeminiyi O ^a   Lindsley, Craig W ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMABILINE; AMARYLLIDACEAE ALKALOID; PYRROLIZIDINE ALKALOID; SUPINIDINE;

ARTICLE; BORAGINACEAE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMARYLLIDACEAE ALKALOIDS; BORAGINACEAE; MOLECULAR STRUCTURE; PYRROLIZIDINE ALKALOIDS; STEREOISOMERISM;

EID: 84859564876     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300466a     Document Type: Article

References (25)

1. Robins, D. J. J. Nat. Prod. Rep. 1989, 6, 221
2. Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1465
3. Dai, W.-M.; Nagao., Y. Heterocycles 1990, 30, 1231-1261
4. Culvenor, C. C. J.; Dowling, D. T.; Edgar, J. A.; Jago, M. V. Ann. N.Y. Acad. Sci. 1969, 163, 837
5. Zalkow, L. H.; Glinski, J. A.; Gelbaum, L. T.; Fleischmann, T. J.; McGowan, L. S.; Gordon, M. M. J. Med. Chem. 1985, 28, 687
6. Suffness, M.; Cordell, G. A. The Alkaloids: Chemistry and Pharmacology, Vol. 25; Brossi, A., Ed.; Academic Press: NY, 1985.
7. Cheeke, P. R. Toxicants of Plant Origins, Vol. 1; Cheeke, P. R., Ed.; CRC Press: FL, 1989.
8. Hartmann, T.; Biller, A.; Witte, L.; Ernst, L.; Boppre, M. Biochem. Syst. Ecol. 1990, 18, 549-556
9. White, L.; Rubiolo, P.; Bicchi, C.; Hartmann, T. Phytochemistry 1993, 32, 187-196
10. Faedyi, O. O.; Senter, T. J.; Hahn, K. N.; Lindsley, C. W. Chem. Eur. J., DOI: 10.1002/chem.201200629.
11. Culvenor, C. C. J.; Smith, L. W. Aust. J. Chem. 1967, 20, 2499-2503
12. El-Shazy, A.; Sarg, T.; Ateya, A.; Aziz, E. A.; Witte, L.; Wink, M. Biochem. Syst. Ecol. 1996, 24, 415-421
13. Roeder, E.; Breitmaier, E.; Birecka, H.; Frohlich, M. W.; Badzies-Crombach, A. Phytochemistry 1991, 30, 1703-1706
14. Likhitwitayawuid, K.; Angerhofer, C. K.; Pezzuto, J. M.; Cordell, G. A.; Ruangrungsi, N. J. Nat. Prod. 1993, 56, 1331
15. Findlay, A. D.; Banwell, M. G. Org. Lett. 2009, 11, 3160-3162
16. Takahata, Banba, Y.; Momose, T. Tetrahedron 1991, 47, 7635-7644
17. Stritzke, K.; Schulz, S.; Nishida, R. Eur. J. Chem. 2002, 3884-3892
18. Brinner, K. M.; Ellman, J. A. Org. Biomol. Chem. 2005, 3, 2109-2113
19. Schulte, M. L.; Lindsley, C. W. Org. Lett. 2011, 13, 5684-5687
20. Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, T. P. J. Org. Chem. 1999, 64, 1278-1284
21. Tang, T. P.; Ellman, J. A. J. Org. Chem. 2002, 67, 7819-7832
22. Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092-1093
23. Brak, K.; Ellman, J. A. J. Am. Chem. Soc. 2009, 131, 3850-3851
24. Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron 1999, 55, 8883-8904
25. Kuhn, K. M.; Champange, T. M.; Hong, S. H.; Wei, W.-H.; Nickel, A.; Lee, C. W.; Virgil, S. C.; Grubbs, R. H.; Pederson, R. L. Org. Lett. 2010, 125, 984-987