The first total synthesis of vinaxanthone, a fungus metabolite possessing multiple bioactivities

Chemistry Letters

Volumn 36, Issue 1, 2007, Pages 10-11

  Tatsuta, Kuniaki ^a   Kasai, Soko ^a   Amano, Yuki ^a   Yamaguchi, Takahiro ^a   Seki, Masashi ^a   Hosokawa, Seijiro ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34247184765     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.10     Document Type: Article

References (13)

1. M. Aoki, Y. Itezono, H. Shirai, N. Nakayama, A. Sakai, Y. Tanaka, A. Yamaguchi, N. Shimma, K. Yokose, H. Seto, Tetrahedron Lett. 1991, 32, 4737.
2. S. K. Wrigley, M. A. Latif, T. M. Gibson, M. I. Chicarelli-Robinson, D. H. Williams, Pure Appl. Chem. 1994, 66, 2383.
3. K. Kumagai, N. Hosotani, K. Kikuchi, T. Kimura, I. Saji, J. Antibiot. 2003, 56, 610.
4. K. Kikuchi, A. Kishino, O. Konishi, K. Kumagai, N. Hosotani, I. Saji, C. Nakayama, T. Kimura, J. Biol. Chem. 2003, 278, 42985.
5. A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856.
6. D. V. Rao, F. A. Stuber, Synthesis 1983, 308.
7. For experimental data of the IMDA reaction and characterization data of all new products, see Supporting Information.
8. H. Saneyoshi, K. Seio, M. Sekine, J. Org. Chem. 2005, 70, 10453.
9. R. F. Heck, Org. React. 1982, 27, 345.
10. Crystallographic data reported in this manuscript have been deposited with Cambridge Crystallographic Data Center as supplementary publication No. CCDC-619253 for compound 12. Copies of the data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Center, 12, Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
11. C. D. Cook, J. Org. Chem. 1953, 18, 261.
12. K. Tatsuta, K. Akimoto, M. Annaka, Y. Ohno, M. Kinoshita, Bull. Chem. Soc. Jpn. 1985, 58, 1699.
13. An authentic sample of natural vinaxanthone was kindly provided by Drs. M. Nakatsuka, T. Kimura, and K. Kumagai, Dainippon Sumitomo Pharma Co., Ltd.