First total synthesis of crispine B by nitro aldol and the Bischler-Napieralski reaction

Heterocycles

Volumn 77, Issue 2, 2009, Pages 1397-1402

  Yasuhara, Tomohisa ^a   Zaima, Naoko ^a   Hashimoto, Satoko ^a   Yamazaki, Masako ^a   Muraoka, Osamu ^a  

^a KINKI UNIVERSITY   (Japan)

Author keywords

Alkaloid; Carduus crispus L; Crispine B; Isoquinoline; Total Synthesis

Indexed keywords

EID: 77955702064     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)104     Document Type: Article

References (22)

1. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley-VCH New York
2. T. Yasuhara, K. Nishimura, M. Yamashita, N. Fukuyama, K. Yamada, O. Muraoka, and K. Tomioka Org. Lett. 5 2003 1123
3. T. Yasuhara, E. Osafune, K. Nishimura, M. Yamashita, K. Yamada, O. Muraoka, and K. Tomioka Tetrahedron Lett. 45 2004 3043
4. T. Yasuhara, K. Nishimura, E. Osafune, O. Muraoka, and K. Tomioka Chem. Pharm. Bull. 52 2004 1109
5. Q. Zhang, G. Tu, Y. Zhao, and T. Cheng Tetrahedron 58 2002 6795
6. W.-D. Xie, P.-L. Li, and Z.-J. Jia Pharmazie 60 2005 233
7. H.-J. Knlker, and S. Agarwal Tetrahedron Lett. 46 2005 1173
8. R. Child, and F.L. Pyman J. Chem. Soc. 1931 36
9. J. Szawkalo, A. Zawadzka, K. Wojtasiewicz, A. Leniewski, J. Drabowicz, and Z. Czarnocki Tetrahedron: Asymmetry 16 2005 3619
10. T.R. Wu, and J.M. Chong J. Am. Chem. Soc. 128 2006 9646
11. N. Meyer, and T. Opatz Eur. J. Org. Chem. 17 2006 3997
12. F.D. King Tetrahedron 63 2007 2053
13. J. Szawkalo, S.J. Czarnocki, A. Zawadzka, K. Wojtasiewicz, A. Leniewski, J.K. Maurin, Z. Czarnocki, and J. Drabowicz Tetrahedron: Asymmetry 18 2007 406
14. S.M. Allin, S.N. Gaskell, J.M.R. Towler, P.C.B. Page, B. Saha, M.J. McKenzie, and W.P. Martin J. Org. Chem. 72 2007 8972
15. F. Xu, B. Simmons, R.A. Reamer, E. Corley, J. Murry, and D. Tschaen J. Org. Chem. 73 2008 312
16. T. Kanemitsu, Y. Yamashita, K. Nagata, and T. Itoh Heterocycles 74 2007 199
17. T. Oriyama, M. Aoyagi, and K. Iwanami Chem. Lett. 36 2007 612
18. A. Bischler Chem. Ber. 26 1893 1891
19. J.P. Wolfe Name Reactions in Heterocyclic Chemistry 2005 John Wiley & Sons, Inc New York 376 385
20. K. Takaba, and J. Kunitomo Yakugaku Zasshi 117 1997 555
21. T.A. Jacob, G.B. Bachman, and H.B. Hass J. Org. Chem. 16 1951 1572
22. T. Fujii, S. Yoshifuji, and K. Yamada Chem. Pharm. Bull. 26 1978 2071