Synthesis of glaziovianin A: A potent antitumor isoflavone

Chemistry Letters

Volumn 36, Issue 11, 2007, Pages 1382-1383

  Hayakawa, Ichiro ^a   Ikedo, Akiyuki ^a   Kigoshi, Hideo ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 36849069399     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.1382     Document Type: Article

References (15)

1. A. Yokosuka, M. Haraguchi, T. Usui, S. Kazami, H. Osada, T. Yamori, Y. Mimaki, Bioorg. Med. Chem. Lett. 2007, 17, 3091.
2. T. Yamori, A. Matsunaga, S. Saito, K. Yamazaki, A. Komi, K. Ishizu, I. Mita, H. Edatsugi, Y. Matsuda, K. Takezawa, O. Nakanishi, H. Kohno, Y. Nakajima, H. Komatsu, T. Andoh, T. Tsuruo, Canser Res. 1999, 59, 4042.
3. K. Komiyama, in Microbial Chemistry, 4th ed., ed. by Y. Ueno, S. Ōmura, Nankodo, Tokyo, 2003, Chap. 7A, pp. 257-274.
4. Y. Hoshino, N. Miyaura, A. Suzuki, Bull. Chem. Soc. Jpn. 1988, 61, 3008.
5. M. A. Rizzacasa, M. V. Sargent, J. Chem. Soc., Perkin Trans. 1 1987, 2017.
6. R. Slamet, D. Wege, J. Chem. Res., Synop 2001, 18.
7. M. Murata, S. Watanabe, Y. Masuda, J. Org. Chem. 1997, 62, 6458.
8. T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508.
9. The methylene acetal unit of compound 4 was hydrolyzed by acidic workup with 1 M HCl to give catechol 10 (Entries 2 and 4), however, compound 10 was not detected in Entries 1 and 3 somehow.
10. R. B. Gammill, Synthesis 1979, 901.
11. Y. Igarashi, H. Kumazawa, T. Ohshima, H. Satomi, S. Terabayashi, S. Takeda, M. Aburada, K. Miyamoto, Chem. Pharm. Bull. 2005, 53, 1088.
12. R. Hong, J. Feng, R. Hoen, G.-q. Lin, Tetrahedron 2001, 57, 8685.
13. K. Ding, S. Wang, Tetrahedron Lett. 2005, 46, 3707.
14. max 317.0 (log ε 4.02), 256.5 nm (4.21), mp 185.0-187.0°C.
15. 50 of 7.9 and 8.3 μM, respectively. These biological assays were carried out by Prof. T. Usui, Graduate School of Life and Environmental Sciences, University of Tsukuba.