First total synthesis of hinckdentine a

Organic Letters

Volumn 11, Issue 1, 2009, Pages 197-199

  Higuchi, Kazuhiro ^a   Sato, Yukihiro ^a   Tsuchimochi, Mei ^a   Sugiura, Kenta ^a   Hatori, Masatoshi ^a   Kawasaki, Tomomi ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HINCKDENTINE A; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; QUINAZOLINES; STEREOISOMERISM;

EID: 59649124244     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802394n     Document Type: Article

References (27)

1. Blackman, A. J.; Hambley, T. W.; Picker, K.; Taylor, W. C.; Thirasasana, N. Tetrahedron Lett. 1987, 28, 5561-5562.
2. Grinev, A. N.; Kurilo, G. N.; Cherkasova, A. A.; Mashkovskii, M. D.; Andreeva, N. I.; Sokolov, I. K. Khim.-Farm. Zh. 1978, 12, 97-101.
3. (a) Billimoria, A. D.; Cava, M. P. J. Org. Chem. 1994, 59, 6777-6782.
4. (b) Barnwell, N.; Beddoes, R. L.; Mitchell, M. B.; Joule, J. A. Heterocycles 1994, 37, 175-179.
5. (c) Domon, L.; Coeur, C. L.; Grelard, A.; Thiéry, V.; Besson, T. Tetrahedron Lett. 2001, 42, 6671-6674.
6. (d) Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571-1578.
7. (e) Mendiola, J.; Castellote, I.; Alvarez-Builla, J.; Fernández-Gadea, J.; Gómez, A.; Vaquero, J. J. J. Org. Chem 2006, 71, 1254-1257.
8. (f) Helliwell, M.; Corden, S.; Joule, J. A. Acta Crystallogr. 2007, E63, o1993-o1995.
9. Liu, Y.; McWhorter, W. W. J. Am. Chem. Soc. 2003, 125, 4240-4252.
10. (a) Witkop, B. J. Am. Chem. Soc. 1950, 72, 614-620.
11. (b) Patrick, J. B.; Witkop, B. J. Am. Chem. Soc. 1950, 72, 633-634.
12. Lednicer, D. L.; Emmert, D. E. J. Heterocycl. Chem. 1970, 6, 575-581.
13. (a) Berti, C.; Greci, L.; Marchetti, L. J. Chem. Soc., Perkin Trans. 2 1979, 233-236.
14. (b) Adam, J.-M.; Winkler, T. Helv. Chim. Acta 1984, 67, 2186-2191.
15. (c) Tommasi, G.; Bruni, P.; Greci, L.; Sgarabotto, P.; Righi, L. J. Chem. Soc., Perkin Trans. 1 1999, 681-686.
16. (d) Liu, Y.; McWhorter, W. W. J. Org. Chem. 2003, 68, 2618-2622.
17. Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 8867-8868.
18. Ardakani, M. A.; Smalley, R. K. Tetrahedron Lett. 1979, 20, 4769-4772.
19. (a) Kawasaki, T.; Ohtsuka, H.; Chien, C.-S.; Omata, M.; Sakamoto, M. Chem. Pharm. Bull. 1987, 35, 1339-1346.
20. (b) Yamada, K.; Kurokawa, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 6630-6331.
21. (c) Higuchi, K.; Masuda, K.; Koseki, T.; Hatori, M.; Sakamoto, M.; Kawasaki, T. Heterocycles 2007, 73, 641-650.
22. Buller, M. J.; Cook, T. G.; Kobayashi, Y. Heterocycles 2007, 72, 163-166.
23. Indole 7 was prepared from 2-nitroacetophenone and phenylhydrazine in 46% two-step yield. MacPhillamy, H. B.; Dziemian, R. L.; Lucas, R. A.; Kuehne, M. E. J. Am. Chem. Soc. 1958, 80, 2172-2178.
24. Batey, R. A.; MacKay, D. B.; Santhakumar, V. J. Am. Chem. Soc. 1999, 121, 5075-5076.
25. Shinada, T.; Ikebe, E.; Oe, K.; Namba, K.; Kawasaki, M.; Ohfune, Y. Org. Lett. 2007, 9, 1765-1767.
26. See Supporting Information.
27. Murahashi, S.-I.; Naota, T.; Saito, E. J. Am. Chem. Soc. 1986, 108, 7846-7847.