Proto- and iodo-lactonization reaction of substituted α,β: γ,δ- unsaturated carboxylic acid

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 7, 1999, Pages 1583-1587

  Kuroda, Chiaki ^a   Tang, Chen Ying ^a   Tanabe, Makoto ^a   Funakoshi, Masabumi ^a  

^a RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; IODINE; LACTONE; SOLVENT;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SOLVATION; SYNTHESIS;

EID: 0032765858     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.1583     Document Type: Article

References (33)

1. B. M. Fraga, Nat. Prod. Rep., 15, 73 (1998); 14, 145 (1997); 13, 307 (1996); 12, 303 (1995); 11, 533 (1994).
2. B. M. Fraga, Nat. Prod. Rep., 15, 73 (1998); 14, 145 (1997); 13, 307 (1996); 12, 303 (1995); 11, 533 (1994).
3. B. M. Fraga, Nat. Prod. Rep., 15, 73 (1998); 14, 145 (1997); 13, 307 (1996); 12, 303 (1995); 11, 533 (1994).
4. B. M. Fraga, Nat. Prod. Rep., 15, 73 (1998); 14, 145 (1997); 13, 307 (1996); 12, 303 (1995); 11, 533 (1994).
5. B. M. Fraga, Nat. Prod. Rep., 15, 73 (1998); 14, 145 (1997); 13, 307 (1996); 12, 303 (1995); 11, 533 (1994).
6. J. M. Cassady and M. Suffness, in "Anticancer Agents Based on Natural Product Models," ed by J. M. Cassady and J. D. Douros, Academic Press, New York (1980), pp. 201-269.
7. a) C. Kuroda, S. Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans. 1, 1990, 519.
8. a) C. Kuroda, S. Shimizu, and J. Y. Satoh, J. Chem. Soc., Chem. Commun., 1987, 286; J. Chem. Soc., Perkin Trans. 1, 1990, 519.
9. b) C. Kuroda, S. Shimizu, T. Haishima, and J. Y. Satoh, Bull. Chem. Soc. Jpn., 66, 2298 (1993).
10. c) C. Kuroda, S. Inoue, S. Kato, and J. Y. Satoh, J. Chem. Res. (S), 1993, 62.
11. d) C. Kuroda, S. Inoue, R. Takemura, and J. Y. Satoh, J. Chem. Soc., Perkin Trans. 1, 1994, 521.
12. e) C. Kuroda and K. Ito, Bull. Chem. Soc. Jpn., 69, 2297 (1996).
13. f) C. Kuroda and S. Anzai, Chem. Lett., 1998, 875.
14. C. Kuroda, N. Mitsumata, and C. Y. Tang, Bull. Chem. Soc. Jpn., 69, 1409 (1996).
15. For examples: a) J. MacMillan and D. A. Taylor, J. Chem. Soc., Perkin Trans. 1, 1985, 837.
16. b) R. K. Boeckman, Jr., D. M. Blum, and S. D. Arthur, J. Am. Chem. Soc., 101, 5060 (1979).
17. c) B. Simonot and G. Rousseau, Tetrahedron Lett., 34, 5723 (1993).
18. d) L. A. Paquette and H. -C. Tsui, Synlett, 1996, 129.
19. e) Y. Shi, L. F. Peng, and Y. Kishi, J. Org. Chem., 62, 5666 (1997).
20. f) K. Mori and T. Umemura, Tetrahedron Lett., 23, 3391 (1982).
21. a) R. W. Hoffmann, R. Stürmer, and K. Harms, Tetrahedron Lett., 35, 6263 (1994).
22. b) J. C. McKew, M. M. Olmstead, and M. J. Kurth, J. Org. Chem., 59, 3389 (1994).
23. c) H. Moon, S. W. E. Eisenberg, M. E. Wilson, N. E. Schore, and M. J. Kurth, J. Org. Chem., 59, 6504 (1994).
24. a) B. Simonot and G. Rousseau, J. Org. Chem., 59, 5912 (1994).
25. b) B. Simonot and G. Rousseau, Tetrahedron Lett., 34, 4527 (1993); F. Homsi and G. Rousseau, J. Org. Chem., 63, 5255 (1998).
26. b) B. Simonot and G. Rousseau, Tetrahedron Lett., 34, 4527 (1993); F. Homsi and G. Rousseau, J. Org. Chem., 63, 5255 (1998).
27. For other recent reports: a) A. C. Royer, R. C. Mebane, and A. M. Swafford, Synlett, 1993, 899.
28. b) J. A. Macritchie, T. M. Peakman, A. Silcock, and C. L. Willis, Tetrahedron Lett., 39, 7415 (1998).
29. F. B. Gonzalez and P. A. Bartlett, Org. Synth., Coll. Vol. 7, 164 (1990).
30. P. A. Bartlett and J. Myerson, J. Am. Chem. Soc., 100, 3950 (1978); see also Ref. 5f.
31. A. G. Schultz and S. J. Kirincich, J. Org. Chem., 61, 5626 (1996).
32. M. A. Brook, C. Henry, R. Jueschke, and P. Modi, Synlett, 1993, 97.
33. C. A. Horiuchi, A. Ikeda, M. Kanamori, H. Hosokawa, T. Sugiyama, and T. T. Takahashi, J. Chem. Res. (S), 1997, 60.