Oxyfunctionalization of unactivated C-H bonds in triterpenoids with tert-butylhydroperoxide catalyzed by meso-5,10,15,20-tetramesitylporphyrinate osmium(II) carbonyl complex

Chemistry and Physics of Lipids

Volumn 163, Issue 2, 2010, Pages 165-171

  Ogawa, Shoujiro ^a   Wakatsuki, Yasuo ^a   Makino, Mitsuko ^a   Fujimoto, Yasuo ^a   Yasukawa, Ken ^a   Kikuchi, Takashi ^a   Ukiya, Motohiko ^a   Akihisa, Toshihiro ^a   Iida, Takashi ^a  

^a NIHON UNIVERSITY   (Japan)

Author keywords

Allylic oxidation; Cytochrome P 450; Hydroxylation; Ketonization; Oxyfunctionalization; Triterpenoid; Unactivated C H bond

Indexed keywords

3 5,10,15,20 TETRAMESITYLPORPHYRINATE OSMIUM CARBONYL; CARBON; HYDROGEN; OSMIUM DERIVATIVE; TERT BUTYL HYDROPEROXIDE; TRITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROXYLATION; MASS FRAGMENTOGRAPHY; OXIDATION; PRIORITY JOURNAL; SEPARATION TECHNIQUE;

CATALYSIS; COORDINATION COMPLEXES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNETIC RESONANCE SPECTROSCOPY; OSMIUM; OXIDATION-REDUCTION; STEREOISOMERISM; TERT-BUTYLHYDROPEROXIDE; TRITERPENES;

EID: 74149084145     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2009.10.012     Document Type: Article

References (34)

1. Amadelli R., Bregola M., Polo E., Carassiti V., and Maldotti A. Photooxidation of hydrocarbons on porphyrin-modified titanium dioxide powders. J. Chem. Soc. Chem. Commun. (1992) 1355-1357
2. Anjaneyulu V., Harischandra Prasad K., Ravi K., and Connolly J.D. Triterpenoids from Mangifera indica. Phytochemistry 24 (1985) 2359-2367
3. Anjaneyulu V., Ravi K., Harischandra Prasad K., and Connolly J.D. Triterpenoids from Mangiferaindica. Phytochemistry 28 (1989) 1471-1477
4. Arasasingham R.D., Balch A.L., Cornman C.R., and Latos-Grazynski L. Dioxygen insertion into iron(III)-carbon bonds. NMR studies of the formation and reactivity of alkylperoxo complexes of iron(III) porphyrins. J. Am. Chem. Soc. 111 (1989) 4357-4363
5. Barr D.P., Martin M.V., Guengerich F.P., and Mason R.P. Reaction of cytochrome P450 with cumene hydroperoxide: ESR spin-trapping evidence for the homolytic scission of the peroxide O-O bond by ferric cytochrome P450 1A2. Chem. Res. Toxicol. 9 (1996) 318-325
6. Bovicelli P., Lupattelli P., Mincione E., Prencipe T., and Curci R. Oxidation of natural targets by dioxiranes. Oxyfunctionalization of steroids. J. Org. Chem. 57 (1992) 2182-2184
7. Breslow R. Enzyme mimics. Pure Appl. Chem. 62 (1990) 1859-1866
8. Breslow R., Zhang X., and Huang Y. Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme. J. Am. Chem. Soc. 119 (1997) 4535-4536
9. Che C.-M., Poon C.-K., Chung W.-C., and Gray H.B. Synthesis and characterization of osmium porphyrins. Inorg. Chem. 24 (1985) 1277-1278
10. Dasgupta A., Goswami A., Ray T.K., Nath A., and Khastgir H.N. Reactions of some triterpenes with mercuric acetate: an unusual reaction with taraxeryl acetate. Indian J. Chem. 19B (1980) 165-168
11. Dias J.R. Mass spectral fragmentation of functionalized lanostanes -1. Mass Spectro. 11 (1976) 333-346
12. Finucane B.W., and Thomson J.B. Direct oxidation of allylic methylene to carbonyl. J. Chem. Soc. D: Chem. Commun. (1969) 1220
13. Gaspar E.M.M., and das Neves H.J.C. Steroidal constituents from mature wheat straw. Phytochemistry 34 (1993) 523-527
14. Gross Z., and Mahammed A. Novel reactivities of iodosylbenzene in the catalytic oxygenation of olefins. J. Mol. Catal. A 142 (1999) 367-372
15. Iida T., Ogawa S., Hosoi K., Makino M., Fujimoto Y., Goto T., Mano N., Goto J., and Hofmann A.F. Regioselective oxyfunctionalization of unactivated carbons in steroids by a model of cytochrome P-450: osmiumporphyrin complex/tert-butylhydroperoxide system. J. Org. Chem. 72 (2007) 823-830
16. Iida T., Ogawa S., Miyata S., Goto T., Mano N., Goto J., and Nambara T. Biomimetic oxidation of unactivated carbons in steroids by a model of cytochrome P-450, oxorutheniumporphyrinate complex. Lipids 39 (2004) 873-880
17. Iida T., Yamaguchi T., Nakamori R., Hikosaka M., Mano N., Goto J., and Nambara T. A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane. J. Chem. Soc., Perkin Trans. 1 (2001) 2229-2236
18. Lindsey J.S., Schreiman I.C., Hsu H.C., Kearney P.C., and Marguerettaz A.M. Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions. J. Org. Chem. 52 (1987) 827-836
19. Makris T.M., von Koenig K., Schlichting I., and Sligar S.G. The status of high-valent metal oxo complexes in the P450 cytochromes. J. Inorg. Biochem. 100 (2006) 507-518
20. Maldotti A., Bartocci C., Amadelli R., Polo E., Battioni P., and Mansuy D. Oxidation of alkanes by dioxygen catalysed by photoactivated iron porphyrins. J. Chem. Soc. Chem. Commun. (1991) 1487-1489
21. Mallavadhani U.V., Narasimhan K., Sudhakar A.V.S., Mahapatra A., Li W., and van Breemen R.B. Three new pentacyclic triterpenes and some flavonoids from the fruits of an Indian ayurvedic plant Dendrophthoe falcate and their estrogen receptor binding activity. Chem. Pharm. Bull. 54 (2006) 740-744
22. Meunier B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem. Rev. 92 (1992) 1411-1456
23. Murahashi S., Naota T., and Komiya N. Metalloporphyrin-catalyzed oxidation of alkanes with molecular oxygen in the presence of acetaldehyde. Tetrahedron Lett. 36 (1995) 8059-8062
24. Ogawa S., Hosoi K., Iida T., Wakatsuki Y., Makino M., Fujimoto Y., and Hofmann A.F. Osmiumporphyrin-catalyzed oxyfunctionalization and isomerization of natural (5β)-bile acids with tert-butylhydroperoxide. Eur. J. Org. Chem. (2007) 3555-3563
25. Ogawa S., Hosoi K., Ikeda N., Makino M., Fujimoto Y., and Iida T. Oxyfunctionalization products of terpenoids with dimethyldioxirane and their biological activity. Chem. Pharm. Bull. 55 (2007) 247-250
26. Ohtake H., Higuchi T., and Hirobe M. The highly efficient oxidation of olefins, alcohols, sulfides and alkanes with heteroaromatic N-oxides catalyzed by ruthenium porphyrins. Heterocycles 40 (1995) 867-903
27. Reese P.B. Remote functionalization reactions in steroids. Steroids 66 (2001) 481-497
28. Saito, S., Matsumoto, T., Tokunaga, Y. Brain function improvers containing steroids. Jpn. Kokai Tokkyo Koho JP 02032022 A (1990).
29. Sejbal J., Klinot J., Buděšínský M., and Protiva J. Functionalization of lupane-3β,28-diyl diacetate with chromium(VI) oxide part 2. Collect. Czech. Chem. Commun. 62 (1997) 1905-1918
30. Shingaki T., Miura K., Higuchi T., Hirobe M., and Nagano T. Regio- and stereo-selective oxidation of steroids using 2,6-dichloropyridine N-oxide catalysed by ruthenium porphyrins. Chem. Commun. (1997) 861-862
31. Sono M., Roach M.P., Coulter E.D., and Dawson J.H. Heme-containing oxygenases. Chem. Rev. 96 (1996) 2841-2887
32. Trotta R.J., Sullivan S.G., and Stern A. Lipid peroxidation and haemoglobin degradation in red blood cells exposed to t-butylhydroperoxide. Biochem. J. 212 (1983) 759-772
33. Yang J., Gabriele B., Belvedere S., Huang Y., and Breslow R. Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes. J. Org. Chem. 67 (2002) 5057-5067
34. Yang J., Weinberg R., and Breslow R. The hydroxylation and amidation of equilenin acetate catalyzed by chloro[5,10,15,20-tetrakis(pentafluorophenyl) porphyrinato]manganese(III). Chem. Commun. (2000) 531-532