Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization

Organic Letters

Volumn 10, Issue 22, 2008, Pages 5211-5214

  Pouységu, Laurent ^a   Marguerit, Mélanie ^a   Gagnepain, Julien ^a   Lyvinec, Gildas ^a   Eatherton, Andrew J ^b   Quideau, Stéphane ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IODOBENZENE; LACTONE; O IODOXYBENZOIC ACID; O-IODOXYBENZOIC ACID; PHENOL DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; WASABIDIENONE B0; WASABIDIENONE B1;

ARTICLE; CATALYSIS; CHEMISTRY; HYDROXYLATION; ISOMERISM; SYNTHESIS;

CATALYSIS; HYDROXYLATION; INDICATORS AND REAGENTS; IODOBENZENES; ISOMERISM; LACTONES; PHENOLS; QUINONES;

EID: 58149201232     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802183p     Document Type: Article

References (35)

1. (a) Quideau, S. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002; p 539.
2. (b) Gagnepain, J.; Méreau, R.; Dejugnac, D.; Léger, J.-M.; Castet, F.; Deffieux, D.; Pouységu, L.; Quideau, S. Tetrahedron 2007, 63, 6493.
3. (a) Waring, A. J. In Advances in Alicyclic Chemistry; Hart, H., Karabatsos, G. J., Eds.; Academic Press: New York and London, 1966; Vol. 1, p 129.
4. (b) Cook, A. H.; Harris, G. J. Chem. Soc. 1950, 1873.
5. (a) Soga, O.; Iwamoto, H.; Oota, Y.; Oiie, Y.; Takuwa, A.; Nozaki, H.; Kuramoto, J.; Nakayama, M. In 27th Symposium on the Chemistry of Natural Products, Hiroshima, 1985, p 687.
6. (b) Soga, O.; Iwamoto, H.; Date, S.; Watanabe, T.; Tanaka, K.; Hata, K.; Takuwa, A.; Nakayama, M. Chem. Lett. 1984, 339.
7. (c) Soga, O.; Iwamoto, H.; Takuwa, A.; Nozaki, H.; Kuramoto, J.; Nakayama, M. Agric. Biol. Chem. 1987, 51, 283.
8. (d) Soga, O.; Iwamoto, H.; Hata, K.; Maeba, R.; Takuwa, A.; Fujiwara, T.; Hsu, Y.-H.; Nakayama, M. Agric. Biol. Chem. 1988, 52, 865.
9. (e) Soga, O.; Iwamoto, H.; Ota, Y.; Odoi, M.; Saito, K.; Takuwa, A.; Nakayama, M. Chem. Lett. 1987, 815.
10. (a) Pedras, M. S. C.; Taylor, J. L.; Morales, V. M. Phytochemistry 1995, 38, 1215.
11. (b) Omolo, J. O.; Anke, H.; Chhabra, S.; Sterner, O. J. Nat. Prod. 2000, 63, 975.
12. (c) Büchi, G.; Francisco, M. A.; Murray, W. V.; Kachholz, T.; Demain, A. L.; Blount, J. F. Tetrahedron Lett. 1983, 24, 2527.
13. (a) Sato, S.; Obara, H.; Yusa, K.; Sudo, K.; Sando, M.; Kagaya, H.; Ijichi, H.; Matsuba, S.; Kumazawa, T.; Onodera, J.-i. Synthesis 1998, 889.
14. (b) Büchi, G.; Francisco, M. A.; Michel, P. Tetrahedron Lett. 1983, 24, 2531.
15. (a) Quideau, S.; Pouységu, L. Org. Prep. Proced. Int. 1999, 31, 617.
16. (b) Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Chem. Rev. 2004, 104, 1383.
17. (c) Quideau, S.; Pouységu, L.; Deffieux, D. Synlett 2008, 467.
18. (a) Ozanne, A.; Pouységu, L.; Depernet, D.; François, B.; Quideau, S. Org. Lett. 2003, 5, 2903.
19. (b) Depernet, D.; François, B. WO 02/057210 Al, U.S. 2002/0107416, PCT/FR02/00189.
20. (a) Lebrasseur, N.; Gagnepain, J.; Ozanne-Beaudenon, A.; Léger, J.-M.; Quideau, S. J. Org. Chem. 2007, 72, 6280.
21. (b) Gagnepain, J.; Castet, F.; Quideau, S. Angew. Chem., Int. Ed. 2007, 46, 1533; 2008, 47, 628.
22. (c) Quideau, S.; Pouységu, L.; Deffieux, D.; Ozanne, A.; Gagnepain, J.; Fabre, I.; Oxoby, M. Arkivoc 2003, 6, 106.
23. (d) Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2002, 4, 285.
24. (a) Goese, M.; Kammhuber, K.; Bacher, A.; Zenk, M. H.; Eisenreich, W. Eur. J. Biochem. 1999, 263, 447.
25. (b) Hecht, S.; Kammhuber, K.; Reiner, J.; Bacher, A.; Eisenreich, W. Phytochemistry 2004, 65, 1057.
26. (c) Abe, N.; Sugimoto, O.; Tanji, K.-i.; Hirota, A. J. Am. Chem. Soc. 2000, 122, 12606.
27. (d) Abe, N.; Arakawa, T.; Yamamoto, K.; Hirota, A. Biosci. Biotechnol. Biochem. 2002, 66, 2090.
28. (a) Gruber, W.; Traub, F. Monatsh. Chem. 1947, 77, 414.
29. (b) Trost, B. M.; Saulnier, M. G. Tetrahedron Lett. 1985, 26, 123.
30. (a) Anelli, P. L.; Montanari, F.; Quici, S. Org. Synth. 1990, 69, 212.
31. (b) Jauch, J.; Czesla, H.; Schurig, V. Tetrahedron 1999, 55, 9787.
32. (c) The (R)-S enantiomer is not commercially available; it can be prepared but in a yield of 24% over eight steps. Tachihara, T.; Ishizaki, S.; Kurobayashi, Y.; Tamura, H.; Ikemoto, Y.; Onuma, A.; Yoshikawa. K.; Yanai, T.; Kitahara, T. Helv. Chim. Acta 2003, 86, 274.
33. (a) Soga, O.; Iwamoto, H.; Takuwa, A.; Takata, T.; Tsugiyama, Y.; Hamada, K.; Fujiwara, T.; Nakayama, M. Chem. Lett. 1988, 1535.
34. (a) Pouységu, L.; Chassaing, S.; Dejugnac, D.; Lamidey, A.-M: Miqueu, K.; Sotiropoulos, J.-M.; Quideau, S. Angew. Chem., Int. Ed. 2008, 47, 3552.
35. (b) Quideau, S.; Fahre, I.; Deffieux, D. Org. Lett. 2004, 6, 4571.