Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids with an iron porphyrin-iodosylbenzene system

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 18, 1996, Pages 2309-2313

  Komuro, Masakatsu ^a   Higuchi, Tsunehiko ^a   Hirobe, Masaaki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343219002     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002309     Document Type: Article

References (21)

1. Part X in the series. Application of Chemical P-450 Model Systems to Study on Drug Metabolism; Part IX, T. Ohe, T. Mashino and M. Hirobe, Tetrahedron Lett., 1995, 36, 7681.
2. For recent reviews: (a) K. E. Harding and T. H. Tiner, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, Oxford, 1991, vol. 4, ch. 1.9;
3. (b) N. Petragnali and H. M. C. Ferraz, Synthesis, 1985, 27.
4. For recent reports: (a) H. Ohtake, T. Higuchi and M. Hirobe, J. Am. Chem. Soc., 1992, 114, 10660;
5. (b) T. Ohe, T. Mashino and M. Hirobe, Arch. Biochem. Biophys., 1994, 310, 402;
6. (c) T. Higuchi, C. Satake and M. Hirobe, J. Am. Chem. Soc., 1995, 117, 8879.
7. (a) M. Komuro, Y. Nagatsu, T. Higuchi and M. Hirobe, Tetrahedron Lett., 1992, 33, 4949;
8. (b) M. Komuro, T. Higuchi and M. Hirobe, Bioorg. Med. Chem., 1995, 3, 55.
9. Preliminary data, restricted to the result of hydroxylactonization of indomethacin, were given in the following paper: M. Hirobe, Pure Appl. Chem., 1994, 66, 729.
10. (a) I. Tabushi and A. Yazaki, J. Am. Chem. Soc., 1981, 103, 7371;
11. (b) I. Tabushi, Coord. Chem. Rev., 1988, 86, 1.
12. T. K. Jones, R. A. Reamer, R. Demond and S. G. Mills, J. Am. Chem. Soc., 1990, 112, 2998.
13. G. Bellucci, H. G. Marioni and A. Marsili, Tetrahedron, 1972, 28, 3393.
14. (a) D. Ostovic and T. C. Bruice, J. Am. Chem. Soc., 1989, 111, 6511;
15. (b) T. G. Traylor, T. Nakano and B. E. Dunlap, J. Am. Chem. Soc., 1986, 108, 2782.
16. A. W. Rettenneier, K. A. Prickett, W. P. Gordon, S. M. Bjorge, S. Chang, R. H. Levy and T. A. Baillie, Drug Metab. Dispos., 1985, 13, 81.
17. R. J. Cregge, J. L. Herrman, C. S. Lee, J. E. Richman and R. H. Schlessinger, Tetrahedron Lett., 1973, 2425.
18. H. Volz and T. Barth, Liebigs Ann. Chem., 1989, 171.
19. H. B. Henbest and B. Nicholls, J. Chem. Soc., 1959, 221.
20. K. Omura and R. Sato, J. Biol. Chem., 1964, 239, 2370.
21. O. H. Lowry, N. J. Rosebrough, A. L. Farr and R. J. Randall, J. Biol. Chem., 1951, 193, 265.