A plausible chemical analogy for biosynthesis of 2-arylbenzofuran of isoflavonoid origin and its application to synthesis of vignafuran

Tetrahedron Letters

Volumn 38, Issue 2, 1997, Pages 259-262

  Kinoshita, Takeshi ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; ISOFLAVONOID;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031021328     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02276-9     Document Type: Article

References (16)

1. Dewick, P. M. Isoflavonoids. In The Flavonoids: Advances in Research since 1986; Harborne, J. B. Ed.; Chapman and Hall: London, 1994; pp. 117-238.
2. Nomura, T. Fortschr. Chem. Org. Naturstoffe 1988, 53, 87-201.
3. Shirata, A.; Takahashi, K.; Takasugi, M.; Nagao, S.; Ishikawa, S.; Ueno, S.; Muñoz, L.; Masamune, T. Sanshi Shikensho Hokoku (Bull. Sericul. Exp. Sta.) 1983, 28, 793-806.
4. Hirano, Y.; Nomura, T.; Ueda, S. Chem. Pharm. Bull. 1989, 37, 554-556.
5. Dewick, P. M. Natural Product Reports 1991, 149-170.
6. Martin, M.; Dewick, P. M. Phytochemistry 1979, 18, 1309-1317.
7. Preston, N. W.; Chamberlain, K.; Skipp, R. A. Phytochemistry 1975, 14, 1843-1844.
8. Deschamps-Vallet, C.; Ilotse, J.-B.; Meyer-Dayan, M.; Molho, D. Tetrahedron Lett. 1979, 1109-1112.
9. Gunning, P. J. M.; Kavanagh, P. J.; Meegan, M. J.; Donnelly, D. M. X. J. Chem. Soc. Perkin 1 1977, 691-694.
10. +, 94), 206 (100).
11. Singer, L. A.; Kong, N. P. J. Am. Chem. Soc. 1966, 88, 5213-5219.
12. 8 118°). [2-d]-2-Hydroxy-isoflav-3-ene was also prepared in the same manner using d-DIBAL.
13. 10
14. 2O) was added to the residue and this mixture was refluxed 3 hr. Workup in the usual manner afforded vignafuran (1) in 56 % yield.
15. McKittrick, B. A.; Scannell, R. T.; Stevenson, R. J. Chem. Soc. Perkin 1 1982, 3017-3020.
16. Watanabe, M.; Kawanishi, K.; Furukawa, S. Chem. Pharm. Bull. 1991, 39, 579-583.