A synthetic study on bauhinoxepin J: Construction of a dibenzo[bf]oxepin ring system by a DDQ-promoted oxidative dearomatization-cyclization approach

Heterocycles

Volumn 80, Issue 1, 2010, Pages 623-629

  Yoshida, Masahiro ^a   Maeyama, Yohei ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Cyclization; Dearomatization; Oxepin; Oxidative Reaction; Quinone

Indexed keywords

EID: 76949106957     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-09-S(S)31     Document Type: Article

References (8)

1. Boonphong S., Puangsombat P., Baramee A., Mahidol C., Ruchirawat S., and Kittakoop P. J. Nat. Prod. 70 (2007) 795
2. For representative examples of the oxidative formation of quinone monoacetals, see:. Miyashita K., Sakai T., and Imanishi T. Org. Lett. 5 (2003) 2683
3. Basler S., Brunck A., Jautelat R., and Winterfeldt E. Helv. Chim. Acta 83 (2000) 1854
4. Danishefsky S., Berman M., Ciufolini M., Etheredge S.J., and Segmuller B.E. J. Am. Chem. Soc. 107 (1985) 3891
5. Poigny S., Guyot M., and Samad M. J. Org. Chem. 63 (1998) 5890
6. McMurry J.E., and Fleming M.P. J. Am. Chem. Soc. 96 (1974) 4708
7. When the DDQ-promoted reaction was carried out under aqueous conditions, the corresponding2-hydroxyphenethyl-substituted p-quinone was obtained in 31% yield. More than 50% of the starting material was recovered when 2equiv of DDQ was subjected to the reaction.
8. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 733689. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 lEZ, UK [fax: +44(0) 1223336033 or e-mail: deposit@ccdc.cam.ac.uk].