A new preparation of 2,5-dihydro-1-benzoxepins using Mitsunobu cyclization, and the synthesis of natural radulanins

Tetrahedron Letters

Volumn 41, Issue 24, 2000, Pages 4787-4790

  Yamaguchi, Seiji ^a   Furihata, Katsunori ^a   Miyazawa, Masahiro ^a   Yokoyama, Hajime ^a   Hirai, Yoshiro ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIHYDRO 1 BENZOXEPIN DERIVATIVE; BENZOXEPIN DERIVATIVE; RADULANIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034660328     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00676-6     Document Type: Article

References (16)

1. (a) Dean, F. M.; Taylor, D. A. H. J. Chem. Soc. (C) 1966, 114.
2. (b) McCabe, P. H.; McCrindle, R.; Murray, D. H. J. Chem. Soc. Chem. Comm. 1967, 145. (c)
3. Eshlett, I. T.; Taylor, D. A. H. J. Chem. Soc. (C) 1968, 481.
4. (d) Takasugi, M.; Nagao, S.; Masamune, T. Tetrahedron Lett. 1979, 4675.
5. (e) Breuer, M.; Leeder, G.; Proksch, P.; Budzikiewicz, H. Phytochemistry 1986, 25, 495.
6. (f) McCormick, S.; Robson, K.; Bohm, B. Phytochemistry 1986, 25, 1723.
7. (g) Asakawa, Y.; Hashimoto, T.; Takikawa, K.; Tori, M.; Ogawa, S. Phytochemistry, 1991, 30, 235.
8. Yamaguchi, S.; Saitoh, A.; Kawase, Y. Bull. Chem. Soc. Jpn. 1986, 59, 3983.
9. Unpublished, but a similar photo-ring expansion of 6-methoxy-2,2,5,7,8-pentamethyl-2H-chromene was reported by: Dallacker, F.; Reperich, K. Chemiker-Zeitung 1991, 115, 306.
10. Stefinovic, M.; Snieckus, V. J. Org. Chem. 1998, 63, 2808.
11. N2 in the Mitsunobu reactions was described by: Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891, and summarized in Organic Reactions; 1992; Vol. 42, p. 335.
12. N2 in the Mitsunobu reactions was described by: Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891, and summarized in Organic Reactions; 1992; Vol. 42, p. 335.
13. Rayner, C. M.; Astle, P. C.; Paquette, L. A. J. Am. Chem. Soc. 1992, 114, 3926.
14. Kamlage, S. Sefkow, M. Peter, M. G. J. Org. Chem. 1999, 64, 2938.
15. Raduranin A: Asakawa, Y.; Toyota, M.; Takemoto, T. Experimentia 1978, 34, 971; Raduranin A methyl ether: Asakawa, Y.; Takeda, R.; Toyota, M.; Takemoto, T. Phytochemistry 1981, 20, 858.
16. Raduranin A: Asakawa, Y.; Toyota, M.; Takemoto, T. Experimentia 1978, 34, 971; Raduranin A methyl ether: Asakawa, Y.; Takeda, R.; Toyota, M.; Takemoto, T. Phytochemistry 1981, 20, 858.