A novel approach to erythrinan alkaloids by utilizing substituted biphenyl as building block

Synlett

Volumn , Issue 4, 2004, Pages 615-618

  Yasui, Yoshizumi ^a   Koga, Yukiko ^a   Suzuki, Keisuke ^a   Matsumoto, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Biphenyl compound; Erythrinan alkaloid; O methylerysodienone; ortho quinone acetal; Spirocyclization

Indexed keywords

1,4 BENZOQUINONE; ACETAL; ALKALOID; BIPHENYL; CARBAMIC ACID; LEWIS ACID; METHYL GROUP; O METHYLERYSODIENONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ERYTHRINA; OXIDATION; SYNTHESIS;

EID: 1642401948     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817753     Document Type: Article

References (32)

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7. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505.
8. For recent synthetic studies, see: (a) Fukumoto, H.; Esumi, T.; Ishihara, J.; Hatakeyama, S. Tetrahedron Lett. 2003, 44, 8047. (b) Shimizu, K.; Takimoto, M.; Mori, M. Org. Lett. 2003, 5, 2323. (c) Gill, C.; Greenhalgh, D. A.; Simpkins, N. S. Tetrahedron Lett. 2003, 44, 7803. (d) Chikaoka, S.; Toyao, A.; Ogasawara, M.; Tamura, O.; Ishibashi, H. J. Org. Chem. 2003, 68, 312. (e) Miranda, L. D.; Zard, S. Z. Org. Lett. 2002, 4, 1135. (f) Allin, S. M.; James, S. L.; Elsegood, M. R. J.; Martin, W. P. J. Org. Chem. 2002, 67, 9464. (g) Padwa, A.; Waterson, A. G. J. Org. Chem. 2000, 65, 235. (h) Hosoi, S.; Nagao, M.; Tsuda, Y.; Isobe, K.; Sano, T.; Ohta, T. J. Chem. Soc., Perkin Trans. 1 2000, 1505.
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28. 2IPh, MeOH] in 37% overall yield (Figure 2). (Equation Presented)
29. 4), and concentrated in vacuo. The residue was purified by PTLC (hexane/EtOAc = 6:4) to give 9 (39.3 mg, 84%) as a colorless oil.
30. 2 in the yield of 9.
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32. Yasui, Y.; Suzuki, K.; Matsumoto, T. Synlett 2004, DOI.