Synthesis of Biologically Active Catecholic Compounds via ortho-Selective Oxygenation of Phenolic Compounds Using Hypervalent Iodine(V) Reagents

Current Organic Synthesis

Volumn 9, Issue 5, 2012, Pages 650-669

  Bernini, Roberta ^a   Fabrizi, Giancarlo ^b   Pouységu, Laurent ^c   Deffieux, Denis ^c   Quideau, Stéphane ^c  

^a UNIVERSITY OF TUSCIA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c INSTITUT DES SCIENCES MOLÉCULAIRES   (France)

Author keywords

2 Iodoxybenzoic acid (IBX); Catechols; Hypervalent iodine(V) reagents; Iodylarenes; Ortho hydroxylation; Ortho quinones; Polymer supported IBX; Stabilized 2 Iodoxybenzoic acid (SIBX)

Indexed keywords

EID: 84867700668     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017912803251792     Document Type: Review

References (282)

1. Quideau, S.; Pouységu, L. Synthetic uses of orthoquinone monoketals and their orthoquinol variants. A review. Org. Prep. Proc. Int., 1999, 31, 617-680.
2. Quideau, S. In: Modern Arene Chemistry; Astruc, D., Ed.; Wiley- VCH, Weinheim, 2002; 539-573.
3. Magdziak, D.; Meek, S. J.; Pettus, T. R. R. Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis. Chem. Rev., 2004, 104, 1383-1429.
4. Pouységu, L.; Deffieux, D.; Quideau, S. Hypervalent iodinemediated phenol dearomatization in natural product synthesis. Tetrahedron, 2010, 66, 2235-2261.
5. Huang, C.; Ghavtadze, N.; Chattopadhyay, B.; Gevorgyan, V. Synthesis of catechols from phenols via Pd-catalyzed silanoldirected C-H oxygenation. J. Am. Chem. Soc., 2011, 133, 17630-17633, and references cited therein.
6. Quideau, S.; Deffieux, D.; Douat-Casassus, C.; Pouységu, L. Plant polyphenols: chemical properties, biological activities, and synthesis. Angew. Chem. Int. Ed., 2011, 50, 586-621.
7. Utkovica, V.; Klasinc, L.; Bors, W. Kinetic study of flavonoid reactions with stable radicals. J. Agric. Food Chem., 2004, 52, 2816-2820.
8. Wang, L.-F.; Zhang, H.-Y. A theoretical study of the different radical-scavenging activities of catechin, quercetin, and a rationally designed planar catechin. Bioorg. Chem., 2005, 33, 108-115.
9. Tejero, I.; Gonzalez-Garcia, N.; Gonzalez-Lafont, A.; Luch, J. M. Tunneling in green tea: understanding the antioxidant activity of catechol-containing compounds. A variational transitionstate theory study. J. Am. Chem. Soc., 2007, 129, 5846-5854.
10. Chen, J. H.; Ho, C.-T. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem., 1997, 45, 2374-2378.
11. Visioli, F.; Galli, C. Olive oil phenols and their potential effects on human health. J. Agric. Food Chem., 1998, 46, 4292-4296.
12. Pietta, P. Flavonoids as antioxidants. J. Nat. Prod., 2000, 63, 1035-1042.
13. Kong, J.-M.; Chia, L.-S.; Goh, N.-K.; Chia, T.-F.; Brouillard, R. Analysis and biological activities of anthocyanins. Phytochemistry, 2003, 64, 923-933.
14. Seyourn, A.; Asres, K.; Kamdeel El-Fiky, F. Structure-radical scavenging activity relationships of flavonoids. Phytochemistry, 2006, 67, 2058-2070.
15. Foti, M. C. Antioxidant properties of phenols. J. Pharm. Pharmacol., 2007, 59, 1673-1685.
16. Kelly, S. L.; Lamb, D. C.; Jackson, C. J.; Warrilow, A. G; Kelly, D. E. The biodiversity of microbial cytochromes P450. Adv. Microb. Physiol., 2003, 47, 131-186.
17. Lewis, D. F. V. 57 Varieties: the human cytochromes P450. Pharmacogenomics, 2004, 5, 305-318.
18. Morant, M.; Bak, S.; Møller, B. L.; Werck-Reichhart, D. Plant cytochromes P450: tools for pharmacology, plant protection and phytoremediation. Curr. Opin. Biotechnol., 2003, 14, 151-162.
19. Halbwirth, H.; Forkmann, G.; Stich, K. The A-ring specific hydroxylation of flavonols in position 6 in Tagetes sp is catalyzed by a cytochrome P450 dependent monooxygenase. Plant Sci., 2004, 167, 129-135.
20. Ayabe, S.-I; Akashi, T. Cytochrome P450 s in flavonoid metabolism. Phytochem. Rev., 2006, 5, 271-282.
21. Halbwirth, H.; Stich, K. An NADPH and FAD dependent enzyme catalyzes hydroxylation of flavonoids in position 8. Phytochemistry, 2006, 67, 1080-1087.
22. Ullrich, R.; Hofrichter, M. Enzymatic hydroxylation of aromatic compounds. Cell. Mol. Life Sci., 2007, 64, 271-293.
23. Urlacher, V. B. In: Handbook of Green Chemistry, Vol. 3: Biocatalysis; Crabtree, R. H., Ed.; Wiley-VCH, Weinheim, 2009; 1-25.
24. Klijn, J. E.; Engberts, J. B. F. N. Fast reactions "on water". Nature, 2005, 435, 746-747.
25. McNulty, J.; Das, P. Highly stereoselective and general synthesis of (E)-stilbenes and alkenes by means of an aqueous Wittig reaction. Eur. J. Org. Chem., 2009, 24, 4031-4035.
26. McNulty, J.; Das, P. Aqueous Wittig reactions of semi-stabilized ylides. A straightforward synthesis of 1,3-dienes and 1,3,5-trienes. Tetrahedron Lett., 2009, 50, 5737-5740.
27. McNulty, J.; Das, P.; McLeod, D. Microwave-assisted, aqueous Wittig reactions: organic-solvent- and protecting-group-free chemoselective synthesis of functionalized alkenes. Chem. Eur. J., 2010, 16, 6756-6760.
28. McNulty, J.; Das, P. A short synthesis of the anti-leukemic sesquiterpene (+)-caparratriene employing aqueous Wittig chemistry. Tetrahedron Lett., 2010, 51, 3197-3199.
29. Holland, H. L. In: Biotransformations I, Vol. 8a; Kelly, D. R., Ed.; Wiley- VCH, Weinheim, 1998; 475-533.
30. Decker, H.; Tuczek, F. Phenoloxidase activity of hemocyanins: Activation, substrate orientation and molecular mechanism. Trends Biochem. Sci., 2000, 25, 392-397.
31. Seo, S. Y.; Sharma, V. K.; Sharma, N. Mushroom tyrosinase: recent prospects. J. Agric. Food Chem., 2003, 51, 2837-2853.
32. Halaouli, S.; Asther, M.; Sigoillot, J. C.; Hamdi, M.; Lomascolo, A. Fungal tyrosinases: new prospects in molecular characteristics, bioengineering and biotechnological applications. J. Appl. Microbiol., 2006, 100, 219-232.
33. Claus, H.; Decker, H. Bacterial tyrosinases. Syst. Appl. Microbiol., 2006, 29, 3-14.
34. Guazzaroni, M.; Pasqualini, M.; Botta, G.; Saladino, R. A novel synthesis of bioactive catechols by layer-by-layer immobilized tyrosinase in an organic solvent medium. ChemCatChem, 2012, 4, 89-99.
35. Guazzaroni, M.; Crestini, C.; Saladino, R. Layer-by-Layer coated tyrosinase: An efficient and selective synthesis of catechols. Bioorg. Med. Chem., 2012, 20, 157-166.
36. Horner, L.; Teichmann, K. H.; Weber, K. H.; Geyer, E. Zur. kenntnis der o-chinone, XXV: darstellung und eigenschaften yon o-chinonen mit elektrophilen substituenten. Chem. Ber., 1965, 98, 1233-1245.
37. Horner, L.; Weber, K.-H. Zur kenntnis der o-chinone, XXVI: neue mono- und dihydroxynaphthochinone. Chem. Ber., 1965, 98, 1246-1251.
38. Zimmer, H.; Lankin, D. C.; Horgan, S. W. Oxidations with potassium nitrosodisulfonate. (Fremy's radicals). Teuber reaction. Chem. Rev., 1971, 71, 229-246.
39. Deya, P. M.; Dopico, M.; Raso, A. G.; Morey, J.; Saa, J. M. On the regioselectivity of the Fremy's salt oxidation of phenols. Tetrahedron, 1987, 43, 3523-3532.
40. Wessely, F.; Sinwel, F. Action of lead tetraacetate on phenols. II. o- Quinols. Monatsh. Chem., 1950, 81, 1055-1070.
41. Ebnöther, A.; Meijer, Th. M.; Schmid, H. Über Eleutherinol, ein natürliches naphtopyron. (Inhaltsstoffe aus Eleutherine bulbosa (Mill.) Urb. VI). Helv. Chim. Acta, 1952, 35, 910-928.
42. Bubb, W. A.; Sternhell, S. The Wessely acetoxylation. Tetrahedron Lett., 1970, 11, 4499-4502.
43. McKillop, A.; Perry, D. H.; Edwards, M.; Antus, S.; Farkas, L.; Nógrádi, M.; Taylor, E. C. Thallium in organic synthesis. XLII. Direct oxidation of 4-substituted phenols to 4,4- disubstituted cyclohexa-2,5-dienones using thallium(III) nitrate. J. Org. Chem., 1976, 41, 282-287.
44. Liotta, D.; Arbiser, J.; Short, J. W.; Saindane, M. Synthesis of the isomeric mono- and bisoxiranylpyrenes. J. Org. Chem., 1983, 48, 2932-2933.
45. Barton, D. H. R.; Brewster, A. G.; Ley, S. V.; Rosenfeld, M. N. Oxidation of phenols to ortho-quinones using diphenylselenininc anhydride. J. Chem. Soc., Chem. Commun., 1976, 985-986.
46. Barton, D. H. R.; Finet, J. P.; Thomas, M. Comparative oxidation of phenols with benzeneseleninic anhydride and with benzeneseleninic acid. Tetrahedron, 1988, 44, 6397-6406.
47. Crandall, J. K.; Zucco, M.; Kirsch, R. S.; Coppert, D. M. The formation of orthoquinones in the dimethyldioxirane oxidation of phenols. Tetrahedron Lett., 1991, 32, 5441-5444.
48. Adam, W.; Shimizu, M. The acid-catalyzed oxidation of methoxybenzenes to p-benzoquinones by dimethyldioxirane. Synthesis, 1994, 6, 560-562.
49. Kochi, J. K. In: Metal-Catalyzed Oxidations of Organic Compounds; Sheldon, R. A., Kochi, J. K., Eds; Academic Press, New York, 1981; 368.
50. Notari, B. Synthesis and catalytic properties of titanium-containing zeolites. Stud. Surf. Sci. Catal., 1988, 37, 413-425.
51. Ganeshpure, P. A.; Sudalai, A.; Satish, S. Oxidation of phenols with molecular oxygen catalysed by [N,N'-bis(2'-pyridinecarboxamido)-1,2-benzene]cobalt(II), chelate. Tetrahedron Lett., 1989, 30, 5929-5932.
52. Kholdeeva, O. A.; Golovin, A. V.; Maksimovskaya, R. I.; Kozhevnikov, I. V. Oxidation of 2,3,6-trimethylphenol in the presence of molybdovanadophosphoric heteropoly acids. J. Mol. Catal., 1992, 75, 235-244.
53. Sheldon, R. A.; Mercier, C.; Chabardes, P. Organometallic chemistry in industrial vitamin A and vitamin E synthesis. Pure Appl. Chem., 1994, 66, 1509-1518.
54. Fujibayashi, S.; Nakayama, K.; Nishiyama, Y.; Ishii, Y. Oxidation of phenols and hydroquinones by dioxygen catalyzed by mixed addenda heteropolyoxometalate on active carbon (NPV6Mo6/C). Chem. Lett., 1994, 1345-1348.
55. Adam, W.; Herrmann, W. A.; Lin, J.; Saha-Moller, C. R. Catalytic oxidation of phenols to p-quinones with the hydrogen peroxide and methyltrioxorhenium(VII) system. J. Org. Chem., 1994, 59, 8281-8283.
56. Saladino, R.; Neri, V.; Mincione, E.; Marini, S.; Coletta, M.; Fiorucci, C.; Filippone, P. A new and efficient synthesis of ortho- and para-benzoquinones of cardanol derivatives by the catalytic system MeReO3-H2O2. J. Chem. Soc., Perkin Trans. I, 2000, 581-586.
57. Krohn, K.; Rieger, H.; Khanbabaee, K. A new synthesis of orthoquinones by transition-metal-mediated oxygenation of phenols with tertbutylhydroperoxide and the Mimoun oxodiperoxo molybdenum complex [Mo(O2)2O]·Py·HMPT. Chem. Ber., 1989, 122, 2323-2330.
58. Krohn, K.; Rieger, H.; Brüggmann, K. Transition metal catalyzed oxidation. VI, Improved method for the oxidation of 1-naphtols to 1,2-naphtoquinones. Synthesis, 1990, 1141-1143.
59. Adam, H.; Khanbabaee, K.; Krohn, K.; Küpke, J.; Rieger, H.; Steingröver, K.; Vinke, I. In: Peroxide Chemistry, Mechanistic and Preparative Aspects of Oxygen Transfer; Adam, W., Ed.; Wiley- VCH, Weinheim, 2000; 469-493.
60. Capdevielle, P.; Maumy, M. Ortho-hydroxylation selective des phenols: I - vers un modele chimique simple des tyrosinases. Tetrahedron Lett., 1982, 23, 1573-1576.
61. Capdevielle, P.; Maumy, M. Ortho-hydroxylation selective des phenols: II - un nouveau systeme catalytique a caractere preparatif. Tetrahedron Lett., 1982, 23, 1577-1580.
62. Reinaud, O.; Capdevielle, P.; Maumy, M. Premiere synthese totale d'une hydroxy-methoxy-quinone: la dihydromaesanine. Tetrahedron Lett., 1985, 26, 3993-3996.
63. Chioccara, F.; Di Gennaro, P.; La Monica, G.; Sebastiano, R.; Rindone, B. Selective orthohydroxylation of phenols in copper(I) complexes. Tetrahedron, 1991, 47, 4429-4434.
64. Sayre, L. M.; Nadkarni, D. V. Electronic coupling matrix elements in acceptor-donor excited states and the effect of charge-transfer character on their radiative rate constants. J. Am. Chem. Soc., 1994, 116, 3157-3158.
65. Goldstein, S.; Czapski, G.; Robani, J. Oxidation of phenol by radiolytically generated. OH and chemically generated SO4.-. A distinction between. OH transfer and Hole oxidation in the photolysis of TiO2 colloid solution. J. Phys. Chem., 1994, 98, 6586-6591.
66. Sun, J.; Meng, X.; Shi, Y.; Wang, R.; Feng, S.; Jiang, D.; Xu, R.; Xiao, F. S. A novel catalyst of Cu-Bi-V-O complex in phenol hydroxylation with hydrogen peroxide. J. Catal., 2000, 193, 199-206.
67. Sorokin, A. B.; Tuel, A. Heterogeneous oxidation of aromatic compounds catalyzed by metallophthalocyanine functionalized silicas. New J. Chem., 1999, 23, 473-476.
68. Thangaraj, A.; Kumar, R.; Ratnasamy, P. Catalytic properties of crystalline titanium silicalites II. Hydroxylation of phenol with hydrogen peroxide over TS-1 zeolites. J. Catal., 1991, 131, 294-297.
69. Reddy, J. S.; Sivasanker, S.; Ratnasamy, P. Hydroxylation of phenol over TS-2, a titanium silicate molecular sieve. J. Mol. Catal., 1992, 71, 373-381.
70. Serrano, D. P.; Li, H.-X.; Davis, M. E. Synthesis of titanium-containing ZSM-48. J. Chem. Soc., Chem. Commun., 1992, 745-747.
71. Tuel, A.; Ben Taarit, Y. Comparison between TS-1 and TS-2 in the hydroxylation of phenol with hydrogen peroxide. Appl. Catal. A: General, 1993, 102, 69-77.
72. Allian, M.; Germain, A.; Cseri, T.; Figueras, F. Catalytic hydroxylation of phenol by hydrogen peroxide. Kinetic study and comparison between solid acids and titanosilicates. Stud. Surf. Sci. Catal., 1993, 78, 455-462.
73. Martens, J. A.; Buskens, P.; Jacobs, P. A. Hydroxylation of phenol with hydrogen peroxide on EUROTS-1 catalyst. Appl. Catal. A: General, 1993, 99, 71-84.
74. Liu, H.; Lu, G.; Guo, Y.; Wang, J. Chemical kinetics of hydroxylation of phenol catalyzed by TS-1/diatomite in fixed-bed reactor. Chem. Eng. J., 2006, 116, 179-186.
75. Maurya, M. R.; Titinchi, J. J.; Chand, S.; Mishra, I. M. Zeolite-encapsulated Cr(III), Fe(III), Ni(II), Zn(II) and Bi(III) salpn complexes as catalysts for the decomposition of H2O2 and oxidation of phenol. J. Mol. Catal. A: Chem., 2002, 180, 201-209.
76. 2+ ion-exchanged Naβ zeolite. Chem. Commun., 2003, 628-629.
77. Dubey, A.; Rives, V.; Kannan, S. Catalytic hydroxylation of phenol over ternary hydrotalcites containing Cu, Ni and Al. J. Mol. Catal. A: Chem., 2002, 181, 151-160.
78. Lee, C. W.; Ahn, D. H.; Wang, B.; Hwang, J. S.; Park, S. E. Hydroxylation of phenol over surface functionalized MCM-41 supported metal catalyst. Microporous Mesoporous Mater., 2001, 44-45, 587-594.
79. Zhang, H.; Zhang, X.; Ding, Y.; Yan, L.; Ren, T.; Suo, J. Hydroxylation of phenol catalyzed by copper Keggin-type heteropoly compounds with hydrogen peroxide. New J. Chem., 2002, 26, 376-377.
80. Xiao, F.; Sun, J.; Meng, R.; Yu, H.; Yuan, H.; Jiang, D.; Qiu, S.; Xu, R. A novel catalyst of copper hydroxyphosphate with high activity in wet oxidation of aromatics. Appl. Catal. A: General, 2001, 207, 267-271.
81. Pekşen, B. B.; Üzelakçil, C.; Güneş, A.; Malay, Ö.; Bayraktar, O. A novel silk fibroin-supported iron catalyst for hydroxylation of phenol. J. Chem. Technol. Biotechnol., 2006, 81, 1218-1224.
82. Letaief, S.; Casal, B.; Aranda, P.; Martin-Luengo, M. A.; Ruiz-Hitzky, E. Fe-containing pillared clays as catalysts for phenol hydroxylation. Appl. Clay Sci., 2003, 22, 263-277.
83. Stang, P. J.; Zhdankin, V. V. Organic polyvalent iodine compounds. Chem. Rev., 1996, 96, 1123-1178.
84. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press, San Diego, 1997.
85. Wirth, T.; Hirt, U. H. Hypervalent iodine compounds: recent advances in synthetic applications. Synthesis 1999, 8, 1271-1287.
86. Ochiai, M. In: Chemistry of Hypervalent Compounds; Akiba, K.-y., Ed.; Wiley-VCH: New York, 1999, 359-387.
87. Zhdankin, V. V.; Stang, P. J. Recent Developments in the Chemistry of Polyvalent Iodine Compounds. Chem. Rev. 2002, 102, 2523-2584.
88. Hypervalent Iodine Chemistry - Modern Developments in Organic Synthesis; Wirth, T. Ed.; Springer-Verlag, Berlin, Heidelberg, 2003; Topics in Current Chemistry, Vol. 224
89. Zhdankin, V. V. Benziodoxole-based hypervalent iodine reagents in organic synthesis. Curr. Org. Synth., 2005, 2, 121-145.
90. Wirth, T. Hypervalent iodine chemistry in synthesis: scope and new directions. Angew. Chem. Int. Ed., 2005, 44 (24), 3656-3665.
91. Moriarty, R. M. Organohypervalent iodine: development, applications, and future directions. J. Org. Chem., 2005, 70, 2893-2903.
92. Zhdankin, V. V.; Stang, P. J. Chemistry of polyvalent o iodine. Chem. Rev., 2008, 108, 5299-5358.
93. Uyanik, M.; Ishihara, K. Hypervalent iodine-mediated oxidation of alcohols. Chem. Commun., 2009, 2086-2099.
94. Brand, J. P.; Fernández González, D.; Nicolai, S.; Waser, J. Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions. Chem. Commun., 2010, 47, 102-115.
95. Quideau, S.; Wirth, T. Hypervalent iodine chemistry. Recent advances and applications. Tetrahedron, 2010, 66, 5737-5738.
96. Tamura, Y.; Yakura, T.; Tohma, H.; Kikuchi, K.; Kita, Y. Hypervalent iodine oxidation of p-alkoxy- and related phenols: a facile and efficient synthesis of p-quinones. Synthesis, 1989, 126-127.
97. Callinan, A.; Chen, Y.; Morrow, G. W.; Swenton, J. S. Spiro-annulated 2,5-cyclohexadienones via oxidation of 2'-alkenyl-p-phenyl phenols with iodobenzene diacetate. Tetrahedron Lett., 1990, 31, 4551-4552.
98. Fleck, A. E.; Hobart, J. A.; Morrow, G. W. Mixed quinone monoketals via iodobenzene diacetate oxidation. Synth. Commun., 1992, 22, 179-187.
99. McKillop, A.; L., M.; Taylor, J. K. A simple and efficient procedure for the preparation of p-quinols by hypervalent iodine oxidation of phenols and phenol tripropylsilyl ethers. J. Chem. Soc., Perkin Trans. 1, 1994, 2047-2048.
100. Quideau, S.; Looney, M. A.; Pouységu, L.; Ham, S.; Birney, D. M. Orthoquinone monoketal chemistry. Experimental and density functional theory studies on orthoquinol acetate rearrangements. Tetrahedron Lett., 1999, 40, 615-618.
101. Pouységu, L.; Chassaing, S.; Dejugnac, D.; Lamidey, A.-M.; Miqueu, K.; Sotiropoulos, J.- M.; Quideau, S. Highly diastereoselective synthesis of orthoquinone monoketals through λ3-iodane-mediated oxidative dearomatization of phenols. Angew. Chem. Int. Ed., 2008, 47, 3552-3555.
102. Ladziata, U.; Zhdankin, V. V. Hypervalent iodine(V) reagents in organic synthesis. Arkivoc, 2006, 9, 26-58.
103. Zhdankin, V. V. Organoiodine(V) reagents in organic synthesis. J. Org. Chem., 2011, 76, 1185-1197.
104. For background information on the hypervalency of the iodine element, see: (a)Musher, J. I. The chemistry of hypervalent molecules. Angew. Chem. Int. Ed., 1969, 8, 54-68.
105. Ochiai, M. In: Hypervalent Iodine Chemistry - Modern Developments in Organic Synthesis; Wirth, T., Ed.; Springer- Verlag, Berlin, Heidelberg, 2003; Topics in Current Chemistry, Vol. 224, 5-68.
106. Sharefkin, J. G.; Saltzman, H. Iodoxybenzene. Org. Synth., Coll. Vol. 5, 1973, 665; Vol. 43, 1963, 65, and references cited therein.
107. Davidson, R. I.; Kropp, P. J. Oxidatively assisted nucleophilic substitution/elimination of alkyl iodides in alcoholic media. A further study. J. Org. Chem., 1982, 47, 1904-1909.
108. Katritzky, A. R.; Duell, B. L.; Dupont Durst, H.; Knier, B. L. Substituted o-iodoso- and o-iodoxybenzoic acids. Synthesis and catalytic activity in the hydrolysis of active phosphorus esters and related systems. J. Org. Chem., 1988, 53, 3972-3978.
109. Bravo, A.; Fontana, F.; Fronza, G.; Minisci, F.; Serri, A. Oxidation of alkyl and aryl iodides, phenylacetaldehyde and alkenes by dimethyldioxirane. Reaction products and mechanism. Tetrahedron Lett., 1995, 36, 6945-6948.
110. Frigerio, M.; Santagostino, M.; Sputore, S. A user-friendly entry to 2-iodoxybenzoic acid (IBX). J. Org. Chem., 1999, 64, 4537-4538.
111. Kazmierczak, P.; Skulski, L.; Kraszkiewicz, L. Syntheses of (diacetoxyiodo)arenes or iodylarenes from iodoarenes, with sodium periodate as the oxidant. Molecules, 2001, 6, 881-891.
112. Kraszkiewicz, L.; Skulski, L. Optimized syntheses of iodylarenes from iodoarenes, with sodium periodate as the oxidant. Part II. Arkivoc, 2003, 6, 120-125.
113. Boeckman, Jr., R. K.; Shao, P.; Mullins, J. J. The Dess-Mrtin periodinane: 1,1,1-triacetoxy-1,1-dihydro-1,2.benziodoxol-3(1H)-one. Org. Synth., Coll. Vol. 10, 2004, 696; Vol. 77, 2000, 141.
114. Willgerodt, C. J. Ueber einige aromatische Jodidchloride. Prakt. Chem., 1886, 33, 154-160.
115. Barton, D. H. R Alcock, N. W.; Sawyer, J. F. Secondary bonding. Part 6. Distorted octahedral geometry in seleninyl dichloride-dioxan(1/1) and iodylbenzene. J. Chem. Soc., Dalton Trans., 1980, 115-120.
116. Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Ley, S. V. A practical catalytic method for the preparation of steroidal 1,4- dien-3-ones by oxygen atom transfer from iodoxybenzene to diphenyl diselenide. J. Chem. Soc., Perkin Trans. 1, 1982, 1947-1952.
117. Barton, D. H. R.; Crich, D. Oxidation of olefins with 2-pyridineseleninic anhydride. Tetrahedron, 1985, 41, 4359-4364.
118. Gleiter, R.; Muller, G. Synthesis of tricyclo[5.4.0.02,undeca-3,5,9-triene. J. Org. Chem., 1988, 53, 3912-3917.
119. Barret, R.; Sabot, J. P.; Pautet, F.; Cerf, P.; Daudon, M. Iodylbenzene, a new epoxidizing agent of the D5-steroids. Oxid. Commun., 1989, 12, 55-58.
120. Barret, R.; Daudon, M. Synthesis of quinonimines with iodoxybenzene. Synth. Commun., 1990, 20, 1543-1549.
121. Iida, T.; Nishida, S.; Chang, F. C.; Niwa, T.; Goto, J.; Nambara, T. A new synthesis of allochenodeoxycholic and allocholic acids. Chem. Pharm. Bull., 1993, 41, 763-765.
122. Tohma, H.; Takizawa, S.; Watanabe, H.; Fukuoka, Y.; Maegawa, T.; Kita, Y. Hypervalent iodine(V)-induced asymmetric oxidation of sulfides to sulfoxides mediated by reversed micelles: novel nonmetallic catalytic system. J. Org. Chem., 1999, 64, 3519-3523.
123. Tohma, H.; Takizawa, S.; Morioka, H.; Maegawa, T.; Kita, Y. Novel catalytic asymmetric sulfoxidation in water using the hypervalent iodine reagent iodoxybenzene. Chem. Pharm. Bull., 2000, 48, 445-446.
124. Hinnan, A.; Du Bois, J. A stereoselective synthesis of (-)-tetrodotoxin. J. Am. Chem. Soc., 2003, 125, 11510-11511.
125. Zhang, C. Iodoxybenzene (PhIO2). Synlett, 2009, 1520-1521.
126. For example, see: (a) Barton, D. H. R.; Godfrey, C. R. A.; Morzycki, J. W.; Motherwell, W. B.; Stobie, A. Observations on the chemistry of the iodoxy group. Tetrahedron Lett., 1982, 23, 957-960.
127. Takata, T.; Tajima, R.; Ando, W. Oxidation of dihydroxyaromatics by hypervalent iodine oxides: a facil quinone synthesis. J. Org. Chem., 1983, 48, 4764-4766.
128. Murali, D.; Rao, G. S. K. Terpenoids. LXXII. Iodoxybenzene oxidation of 1-naphthols: synthesis of mansonone A. Indian J. Chem., Sect. B, 1987, 26, 668-670.
129. Reddy, N. K.; Rao, G. S. K. Terpenoids. Part LXXX. Synthesis of 4- isopropyl-1,6-dimethyl-5,8-naphthoquinone (cadalenequinone). Indian J. Chem., Sect. B, 1987, 26, 920-922.
130. Barret, R.; Daudon, M. An efficient synthesis of Juglone. Synth. Commun., 1990, 20, 2907-2912.
131. Macikenas, D.; Skrzypczak-Jankun, E.; Protasiewicz, J. D. Redirecting secondary bonds to control molecular and crystal properties of an iodosyland an iodylbenzene. Angew. Chem. Int. Ed., 2000, 39, 2007-2010.
132. Wirth, T.; Hirt, U. H. Chiral hypervalent iodine compounds. Tetrahedron: Asymmetry, 1997, 8, 23-26.
133. Hirt, U. H.; Spingler, B.; Wirth, T. New chiral hypervalent iodine compounds in asymmetric synthesis. J. Org. Chem., 1998, 63, 7674-7679.
134. Hirt, U. H.; Schuster, M. F. H.; French, A. N.; Wiest, O. G.; Wirth, T. Chiral hypervalent organo-iodine(III) compounds. Eur. J. Org. Chem., 2001, 8, 1569-1579.
135. Zhdankin, V. V.; Koposov, A. Y.; Netzel, B. C.; Yashin, N. V.; Rempel, B. P.; Ferguson, M. J.; Tykwinski, R. R. IBX amides: a new family of hypervalent iodine reagents. Angew. Chem. Int. Ed., 2003, 42, 2194-2196.
136. Ladziata, U.; Carlson, J.; Zhdankin, V. V. Synthesis and oxidative reactivity of new chiral hypervalent iodine(V) reagents based on (S)-proline. Tetrahedron Lett., 2006, 47, 6301-6304.
137. Ladziata, U.; Zhdankin, V. V. N-(2- Iodylphenyl)acylamides - New pentavalent iodine oxidizing reagents. Synlett, 2007, 527-537.
138. Zhdankin, V. V.; Litvinov, D. N.; Koposov, A. Y.; Luu, T.; Fergusson, M. J.; McDonald, R.; Tykwinski, R. R. Preparation and structure of 2- iodoxybenzoate esters: soluble and stable periodinane oxidizing reagents. Chem. Commun., 2004, 106-107.
139. Zhdankin, V. V.; Koposov, A. Y.; Litvinov, D. N.; Ferguson, M. J.; McDonald, R.; Luu, T.; Tykwinski, R. R. Esters of 2-iodoxybenzoic acid: hypervalent iodine oxidizing reagents with a pseudobenziodoxole structure. J. Org. Chem., 2005, 70, 6484-6491.
140. Koposov, A. Y.; Karimov, R. R.; Geraskin, I. M.; Nemykin, V. N.; Zhdankin, V. V. 2-Iodylphenol ethers: preparation, X-ray crystal structure, and reactivity of new hypervalent iodine(V) oxidizing reagents. J. Org. Chem., 2006, 71, 8452-8458.
141. Koposov, A. Y.; Litvinov, D. N.; Zhdankin, V. V. 2- Iodoxybenzenesulfamides: new pseudobenziodoxole-based hypervalent iodine reagents. Tetrahedron Lett., 2004, 45, 2719-2721.
142. Zhdankin, V. V.; Goncharedo, R. N.; Litvinov, D. N.; Koposov, A. Y. Derivatives of 2- iodoxybenzenesulfonic acid: new pseudocyclic hypervalent iodine reagents. Arkivoc, 2005, 4, 8-18.
143. Koposov, A. Y.; Nemykin, V. N.; Zhdankin, V. V. Intra- and intermolecular interactions in the solid state structure of 2- iodylbenzenesulfonamides: a heptacoordinated organic iodine(V) compound. New J. Chem., 2005, 29, 998-1000.
144. Mailyan, A. K.; Geraskin, I. M.; Nemykin, V. N.; Zhdankin, V. V. Preparation, X-ray structure, and oxidative reactivity of N-(2-iodylphenyl)tosylamides and 2-iodylphenyl tosylate: iody larenes stabilized by ortho-substitution with a sulfonyl group. J. Org. Chem., 2009, 74, 8444-8447.
145. Meprathu, B. V.; Justik, M. W.; Protasiewicz, J. D. ortho-Phosphoryl stabilized hypervalent iodosyl- and iodyl-benzene reagents. Tetrahedron Lett., 2005, 46, 5187-5190.
146. Boppisetti, J. K.; Birman, V. B. Asymmetric oxidation of o-alkylphenols with chiral 2-(o-iodoxyphenyl)-oxazolines. Org. Lett., 2009, 11, 1221-1223.
147. Hartmann, C.; Meyer, V. Ueber jodobenzoësäure. Ber. Dtsch. Chem. Ges., 1893, 26, 1727-1732.
148. Askenasy, P.; Meyer, V. Ueber die jodosoverbindungen. Ber. Dtsch. Chem. Ges., 1893, 26, 1354-1370.
149. Wirth, T. IBX-New reactions with an old reagent. Angew. Chem. Int. Ed., 2001, 40, 2812-2814.
150. Satam, V.; Harad, A.; Rajule, R.; Pati, H. 2- Iodoxybenzoic acid (IBX): an efficient hypervalent iodine reagent. Tetrahedron, 2010, 66, 7659-7706.
151. Duschek, A.; Kirsch, S. F. 2-Iodoxybenzoic acid. A simple oxidant with a dazzling array of potential applications. Angew. Chem. Int. Ed., 2011, 50, 1524-1552.
152. Lapitskaya, M. A.; Vasiljeva, L. L.; Pivnitsky, K. K. o-Iodoxybenzoic acid in dimethylformamide as a convenient reagent for the oxidation of alcohols to aldehydes and ketones. Mendeleev Commun., 2008, 18, 309-311.
153. Plumb, J. B.; Harper, D. J. 2-Iodoxbenzoic acid. Chem. Eng. News, 1990, 68, 3.
154. Gougoutas, J. Z. ortho-Iodoxybenzoic acid. Cryst. Struct. Commun., 1981, 10, 489-494.
155. Stevenson, P. J.; Treacy, A. B.; Nieuwenhuyzen, M. Preparation of Dess-Martin periodinane. The role of the morphology of 1- hydroxy-1,2-benziodoxol-3-(1H)-one 1-oxide precursor. J. Chem. Soc., Perkin Trans. 2, 1997, 589-591.
156. Dess, B. D.; Martin, J. C. Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem., 1983, 48, 4155-4156.
157. Dess, B. D.; Martin, J. C. A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species. J. Am. Chem. Soc., 1991, 113, 7277-7287.
158. Frigerio, M.; Santagostino, M. A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO. Tetrahedron Lett., 1994, 35, 8019-8022.
159. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. Oxidation of alcohols with o-iodoxybenzoic acid in DMSO: a new insight into an old hypervalent iodine reagent. J. Org. Chem., 1995, 60, 7272-7276.
160. Nicolaou, K. C.; Zhong, Y.L.; Baran, P. S. New synthetic technology for the rapid construction of novel heterocycles. 1. The reaction of Dess-Martin periodinane with anilides and related compounds. Angew. Chem. Int. Ed., 2000, 39, 622-625.
161. Nicolaou, K. C.; Zhong, Y.L.; Baran, P. S. New synthetic technology for the rapid construction of novel heterocycles. 2. The reaction of IBX with anilides and related compounds. Angew. Chem. Int. Ed., 2000, 39, 625-628.
162. Nicolaou, K. C.; Zhong, Y.L.; Baran, P. S. A new method for the one-step synthesis of α,β-unsaturated carbonyl systems from saturated alcohols and carbonyl compounds. J. Am. Chem. Soc., 2000, 122, 7596-7597.
163. Nicolaou, K. C.; Baran, P. S.; Kranich, R.; Zhong, Y.L.; Sugita, K.; Zou, N. Mechanistic studies of periodinane-mediated reactions of anilides and related systems. Angew. Chem. Int. Ed., 2001, 40, 202-206.
164. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y.L. New synthetic technology for the construction of N-containing quinones and derivatives thereof: total synthesis of epoxyquinomycin B. Angew. Chem. Int. Ed., 2001, 40, 207-210.
165. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.L. Selective oxidation at carbon adjacent to aromatic systems with IBX. J. Am. Chem. Soc., 2001, 123, 3183-3185.
166. Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Modulation of the reactivity profile of IBX by ligand complexation: ambient temperature dehydrogenation of aldehydes and ketones to α,β-unsaturated carbonyl compounds. Angew. Chem. Int. Ed., 2002, 4, 993-996.
167. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.L.; Sugita, K. Iodine(V) reagents in organic synthesis. Part 1. Synthesis of polycyclic heterocycles via Dess??Martin periodinane-mediated cascade cyclization: generality, scope, and mechanism of the reaction. J. Am. Chem. Soc., 2002, 124, 2212-2220.
168. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y.L. Iodine(V) reagents in organic synthesis. Part 2. Access to complex molecular architectures via Dess-Martin periodinane-generated o-imidoquinones. J. Am. Chem. Soc., 2002, 124, 2221-2232.
169. Nicolaou, K. C.; Baran, P. S.; Zhong, Y.L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. Iodine(V) reagents in organic synthesis. Part 3. New routes to heterocyclic compounds via o-iodoxybenzoic acidmediated cyclizations: generality, scope, and mechanism. J. Am. Chem. Soc., 2002, 124, 2233-2244.
170. Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.L. Iodine(V) reagents in organic synthesis. Part 4. o- Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes. J. Am. Chem. Soc., 2002, 124, 2245-2258.
171. Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen- and sulfur-containing substrates: scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections. J. Am. Chem. Soc., 2004, 126, 5192-5201.
172. Thottumkara, A. P.; Vinod, T. K. Synthesis and oxidation reactions of a user- and eco-friendly hypervalent iodine reagent. Tetrahedron Lett., 2002, 43, 569-572.
173. Kommreddy, A.; Bowsher, M. S.; Gunna, M. R.; Botha, K.; Vinod, T. K. Expedient synthesis and solvent dependent oxidation behavior of a water-soluble IBX derivative. Tetrahedron Lett., 2008, 49, 4378-4382.
174. Moorthy, J. N.; Singhal, N.; Senapati, K. Modified o-methyl-substituted IBX: room temperature oxidation of alcohols and sulfides in common organic solvents. Tetrahedron Lett., 2008, 49, 80-84.
175. Moorthy, J. N.; Senapati, K.; Parida, K. N.; Jhulki, S.; Sooraj, K.; Nair, N. N. Twist does a twist to the reactivity: stoichiometric and catalytic oxidations with twisted tetramethyl- IBX. J. Org. Chem., 2011, 76, 9593-9601.
176. Richardson, R. D.; Zayed, J. M.; Altermann, S.; Smith, D.; Wirth, T. Tetrafluoro-IBA and-IBX: hypervalent iodine reagents. Angew. Chem. Int. Ed., 2007, 46, 6529-6532.
177. Stickley, S. H.; Martin, J. C. A mild 10-I-41 Lodinane oxide oxidant for primary and secondary alcohols. Tetrahedron Lett., 1995, 36, 9117-9120.
178. Miura, T.; Nakashima, K.; Tada, N.; Itoh, A. An effective and catalytic oxidation using recyclable fluorous IBX. Chem. Commun., 2011, 47, 1875-1877.
179. Koposov, A. Y.; Litvinov, D. N.; Zhdankin, V. V.; Ferguson, M. J.; McDonald, R.; Tykwinski, R. R. Preparation and reductive decomposition of 2-iodoxybenzenesulfonic acid; X-ray crystal structure of 1H-1-hydroxy-1,2,3-benziodoxathiole 3,3-dioxide. Eur. J. Org. Chem., 2006, 4791-4795.
180. Uyanik, M.; Ishihara, K. 2-Iodoxybenzenesulfonic acid (IBS) catalyzed oxidation of alcohols. Aldrichim. Acta, 2010, 43, 83-91.
181. Zhdankin, V. V.; Smart, J. T.; Zhao, P.; Kiprof, P. Synthesis and reactions of amino acid-derived benziodazole oxides: new chiral oxidizing reagents. Tetrahedron Lett., 2000, 41, 5299-5302.
182. Zhdankin, V. V.; Nemykin, V. N.; Karimov, R. R.; Kazhkenov, Z.-G. Preparation and X-ray crystal structure of 2-iodyl-N,N-dialkylaniline oxides: first entry into the heterocyclic system of benziodoxazole. Chem. Commun., 2008, 6131-6133.
183. Moorthy, J. N.; Senapati, K.; Parida, K. N. 6-Membered pseudocyclic IBX acids: syntheses, X-ray structural sharacterizations, and oxidation reactivities in common organic solvents. J. Org. Chem., 2010, 75, 8416-8421.
184. Quideau, S.; Lyvinec, G.; Marguerit, M.; Bathany, K.; Ozanne-Beaudenon, A.; Buffeteau, T.; Cavagnat, D.; Chénedé, A. Asymmetric hydroxylative phenol dearomatization via in situ generation of iodanes from chiral iodoarenes and m-CPBA. Angew. Chem. Int. Ed., 2009, 48, 4605-4609.
185. Ngatimin, M.; Lupton, D. W. The discovery of catalytic enantioselective polyvalent iodine mediated reactions. Aust. J. Chem., 2010, 63, 653-658.
186. More, J. D.; Finney, N. S. A simple and advantageous protocol for the oxidation of alcohols with o-iodoxybenzoic acid (IBX). Org. Lett., 2002, 4, 3001-3003.
187. Van Arman, S. A. 2-Methyl-2-propanol as solvent for o-iodoxybenzoic acid (IBX) oxidation of 1° alcohols to aldehydes. Tetrahedron Lett., 2009, 50, 4693-4695.
188. Surendra, K.; Srilakshmi Hrishnaveni, N.; Arjun Reddy, M.; Nageswar, Y. V. D.; Rama Rao, K. Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in water/acetone mixture in the presence of β-cyclodextrin. J. Org. Chem., 2003, 68, 2058-2059.
189. Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. A mild, chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as catalyst. J. Org. Chem., 2003, 68, 5422-5425.
190. Kuhakarn, C.; Kittigowittana, K.; Ghabkham, P.; Pohmakotr, M.; Reutrakul, V. Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in a water/CH2Cl2 mixture in the presence of phase-transfer catalyst. Synth. Commun., 2006, 36, 2887-2892.
191. Liu, Z.; Chen, Z.-C.; Zheng, Q.-G. Mild oxidation of alcohols with oiodoxybenzoic acid (IBX) in ionic liquid 1-butyl-3-methyl-imidazolium chloride and water. Org. Lett., 2003, 5, 3321-3323.
192. Chhikara, B. S.; Chandra, R.; Tandon, V. IBX in an ionic liquid: eco-friendly oxidation of 17α-methylandrostan-3β,17β-diol, an intermediate in the synthesis of anabolic oxandrolone. Tetrahedron Lett., 2004, 45, 7585-7588.
193. Thottumkara, A. P.; Bowsher, M. S.; Vinod, T. K. In situ generation of oiodoxybenzoic acid (IBX) and the catalytic use of it in oxidation reactions in the presence of oxone as a co-oxidant. Org. Lett., 2005, 7, 2933-2936.
194. Schulze, A.; Giannis, A. Oxidation of alcohols with catalytic amounts of IBX. Synthesis, 2006, 257-260.
195. Bulman Page, P. C.; Appleby, L. F.; Buckley, B. R.; Allin, S. M.; McKenzie, M. J. In situ generation of 2- iodoxybenzoic acid (IBX) in the presence of tetraphenylphosphonium monoperoxysulfate (TPPP) for the conversion of primary alcohols into the corresponding aldehydes. Synlett, 2007, 10, 1565-1568.
196. Ojha, L. R.; Kudugunti, S.; Maddukuri, P. P.; Kommareddy, A.; Gunna, M. R.; Dokuparthi, P.; Gottam, H. B.; Botha, K. K.; Parapati, D. R.; Vinod, T. K. Benzylic carbon oxidation by an in situ formed o-iodoxybenzoic acid (IBX) derivative. Synlett, 2009, 117-121.
197. Depernet, D.; François, B. WO 02/057210 A1, PCT/FR02/00189, US 2002/0107416; Chem. Abstr., 2002, 137, 109123. NB: Explosive tests were negative in compliance with the 92/69-A14 EEC directive
198. Ozanne, O.; Pouységu, L.; Depernet, D.; François, B.; Quideau, S. A stabilized formulation of IBX (SIBX) for safe oxidation reactions including a new oxidative demethylation of phenolic methyl aryl ethers. Org. Lett., 2003, 5, 2903-2906.
199. Ozanne-Beaudenon, A.; Quideau, S. Safe oxidation of sulfides into sulfoxides using SIBX. Tetrahedron Lett., 2006, 47, 5869-5873.
200. Quideau, S.; Chénedé, A. Stabilized 2-Iodoxybenzoic Acid (SIBX). In: Encyclopedia of Reagents for Organic Synthesis (Online); John Wiley & Sons Ltd., 2012, March 15, DOI: 10.1002/047084289X.rn01376.
201. Sorg, G.; Mengel, A.; Jung, G.; Rademann, J. Oxidizing polymers: a polymer-supported, recyclable hypervalent iodine(V) reagent for the efficient conversion of alcohols, carbonyl compounds, and unsaturated carbamates in solution. Angew. Chem. Int. Ed., 2001, 40, 4395-4397.
202. Mülbaier, M.; Giannis, A. The synthesis and oxidative properties of polymer-supported IBX. Angew. Chem. Int. Ed., 2001, 40, 4393-4394.
203. Reed, N. N.; Delgado, M.; Hereford, K.; Clapham, B.; Janda, K. D. Preparation of soluble and insoluble polymer supported IBX reagents. Bioorg. Med. Chem. Lett., 2002, 12, 2047-2049.
204. Mülbaier, M.; Giannis, A. First synthesis and oxidative properties of polymer-supported IBX. Arkivoc, 2003, 6, 228-236.
205. Lei, Z. Q; Ma, H. C.; Zhang, Z.; Yang, Y. X. Synthesis and oxidation reactions of a polymer-supported IBX reagent. React. Funct. Polym., 2006, 66, 840-844.
206. Lei, Z.; Denecker, C.; Jegasothy, S.; Sherrington, D. C.; Slater, N. K. T.; Sutherland, A. J. A facile route to a polymer-supported IBX reagent. Tetrahedron Lett., 2003, 44, 1635-1637.
207. Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX). Org. Lett., 2002, 4, 285-288.
208. Quideau, S.; Pouységu, L.; Deffieux, D.; Ozanne, A.; Gagnepain, J.; Fabre, I.; Oxoby, M. Iodane-mediated and electrochemical oxidative transformations of 2-methoxy- and 2-methylphenols. Arkivoc, 2003, 6, 106-119.
209. Lebrasseur, N.; Gagnepain, J.; Ozanne-Beaudenon, A.; Léger, J.-M.; Quideau, S. Efficient access to orthoquinols and their [4 +2] cyclodimers via SIBX-mediated hydroxylative phenol dearomatization. J. Org. Chem., 2007, 72, 6280-6283.
210. Gagnepain, J.; Méreau, R.; Dejugnac, D.; Léger, J.-M.; Castet, F.; Deffieux, D.; Pouységu, L.; Quideau, S. Regio- and stereoselectivities in Diels-Alder cyclodimerizations of orthoquinonoid cyclohexa-2,4- dienones. Tetrahedron, 2007, 63, 6493-6505.
211. Gagnepain, J.; Castet, F.; Quideau, S. Total synthesis of (+)-aquaticol by biomimetic phenol dearomatization: double diastereofacial differentiation in the Diels-Alder dimerization of orthoquinols with a C2-symmetric transition state. Angew. Chem. Int. Ed., 2007, 46, 1533-1535.
212. Pouységu, L.; Marguerit, M.; Gagnepain, J.; Lyvinec, G.; Eatherton, A. J.; Quideau, S. Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization. Org. Lett., 2008, 10, 5211-5214.
213. Quideau, S.; Pouységu, L.; Deffieux, D. Oxidative dearomatization of phenols: why, how and what for? Synlett, 2008, 467-495.
214. Quideau, S.; Pouységu, L.; Ozanne, A.; Gagnepain, J. Oxidative dearomatization of phenols and anilines via l3- and l5-iodane-mediated phenylation and oxygenation. Molecules, 2005, 10, 201-216.
215. Pouységu, L.; Sylla, T.; Garnier, T.; Rojas, L. B.; Charris, J.; Deffieux, D.; Quideau, S. Hypervalent iodine-mediated oxygenative phenol dearomatization reactions. Tetrahedron, 2010, 66, 5908-5917.
216. Yuan, Y.; Men, H.; Lee, C. Total synthesis of kendomycin: a macro-Cglycosidation approach. J. Am. Chem. Soc., 2004, 126, 14720-14721.
217. Smith, A. B.; Mesaros, E. F.; Meyer, E. A. Total synthesis of (+)- kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis synthetic strategy. J. Am. Chem. Soc., 2005, 127, 6948-6949.
218. Smith, A. B.; Mesaros, E. F.; Meyer, E. A. Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy. J. Am. Chem. Soc., 2006, 128, 5292-5299.
219. Lowe, J. T.; Panek, J. S. Total synthesis of (-)-kendomycin. Org. Lett., 2008, 10, 3813-3816.
220. Kuboki, A.; Yamamoto, T.; Ohira, S. Total synthesis of (±)-siphanol, a novel cyclooxygenase-inhibitory stilbenolignan. Chem. Lett., 2003, 32, 420-421.
221. Kuboki, A.; Yamamoto, T.; Taira, M.; Arishige, T.; Ohira, S. Total synthesis of (±)-nitidanin and novel procedures for determination of the location of the side chains on 1,4-benzodioxane. Tetrahedron Lett., 2007, 48, 771-774.
222. Kuboki, A.; Maeda, C.; Arishige, T.; Kuyama, K.; Hamabata, M.; Ohira, S. Total synthesis of cleomiscosin C via a regioselective cycloaddition reaction of o-quinone. Tetrahedron Lett., 2008, 49, 4516-4518.
223. Montedoro, G.; Servili, M.; Baldioli, M.; Miniati, E. Simple and hydrolyzable phenolic compounds in virgin olive oil. 1. Their extraction, separation, and quantitative and semiquantitative evaluation by HPLC. J. Agric. Food Chem., 1992, 40, 1571-1576.
224. Montedoro, G.; Servili, M.; Baldioli, M.; Miniati, E. E. Simple and hydrolyzable phenolic compounds in virgin olive oil. 2. Initial characterization of the hydrolyzable fraction. J. Agric. Food Chem., 1992, 40, 1577-1580.
225. Manna, C.; Della Ragione, F.; Cucciola, V.; Borriello, A.; D'Angelo, S.; Galletti, P.; Zappia, V. Biological effects of hydroxytyrosol, a polyphenol from olive oil endowed with antioxidant activity. Adv. Exp. Med. Biol., 1999, 472,115-130.
226. Capasso, R.; Evidente, A.; Avolio, S.; Solla, F. A highly convenient synthesis of hydroxytyrosol and its recovery from agricultural waste waters. J. Agric. Food Chem., 1999, 47, 1745-1748.
227. Ferdinando-Bolanos, J.; Rodriguez, G.; Rodriguez, R.; Heredia, A.; Guillen, R.; Jimenez, A. Production in large quantities of highly purified hydroxytyrosol from liquid-solid waste of two-phase olive oil processing or "alperujo". J. Agric. Food Chem., 2002, 50, 6804-6811.
228. Allouche, N.; Fki, I.; Sayadi, S. Toward a high yield recovery of antioxidants and purified hydroxytyrosol from olive mill wastewaters. J. Agric. Food Chem., 2004, 52, 267-273.
229. Visioli, F.; Bellomo, G.; Galli, C. Free radical-scavenging properties of olive oil polyphenols. Biochem. Biophys. Res. Commun., 1998, 247, 60-64.
230. O'Dowd, Y.; Driss, F.; Dang, P. M.; Elbim, C.; Gougerot-Pocidalo, M. A.; Pasquier, C.; El-Benna, J. Antioxidant effect of hydroxytyrosol, a polyphenol from olive oil: scavenging of hydrogen peroxide but not superoxide anion produced by human neutrophils. Biochem. Pharmacol., 2004, 68, 2003-2008.
231. Salami, M.; Galli, C. De Angelis, L.; Visioli, F. Formation of F2- isoprostanes in oxidized low density lipoprotein: inhibitory effect of hydroxytyrosol. Pharmacol. Res., 1995, 31, 275-279.
232. Carluccio, M. A.; Siculella, L.; Ancora, M. A.; Massaro, M.; Scoditti, E.; Storelli, C.; Visioli, F.; Distante A.; De Caterina, R. Olive oil and red wine antioxidant polyphenols inhibit endothelial activation. Arterioscler. Thromb. Vasc. Biol., 2003, 23, 622-629.
233. Maiuri, M. C.; De Stefano, D.; Di Meglio, P.; Irace, C.; Savarese, M.; Sacchi, R.; Cinelli, M. P.; Carnuccio, R. Hydroxytyrosol, a phenolic compound from virgin olive oil, prevents macrophage activation. Naunyn- Schmiedeberg's Arch. Pharmacol., 2005, 371, 457-465.
234. Visioli, F.; Bellomo, G.; Montedoro, C.; Galli, C. Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. Atherosclerosis, 1995, 117, 25-32.
235. Della Ragione, F.; Cucciolla, V. Borriello, A.; Della Pietra, V.; Pontoni, G.; Racioppi, L.; Manna, C.; Galletti, P.; Zappia, V. Hydroxytyrosol, a natural molecule occurring in olive oil, induces cytochrome c-dependent apoptosis. Biochem. Biophys. Res. Commun., 2000, 278, 733-739.
236. Fabiani, R.; De Bartolomeo, A.; Rosignoli, P.; Servili, M.; Montedoro, G. F.; Morozzi G. Cancer chemprevention by hydroxytyrosol isolated from virgin olive oil through G1 cell cycle arrest and apoptosis. Eur. J. Cancer Prev., 2002, 11, 351-358.
237. Corona, G.; Deiana, M.; Incani, A.; Vauzour, D.; Dessì, M. A.; Spencer, J. P. Inhibition of p38/CREB phosphorylation and COX-2 expression by olive oil polyphenols underlies their anti-proliferative effects. Biochem. Biophys. Res. Commun., 2007, 362, 606-611.
238. Kip1 and with induction of differentiation in HL60 cells. J. Nutr., 2008, 42-48.
239. Corona, G.; Deiana, M.; Incani, A.; Vauzour, D.; Dessì, M.A.; Spencer, J. P. Hydroxytyrosol inhibits the proliferation of human colon adenocarcinoma cells through inhibition of ERK1/2 and cyclin D1. Mol. Nutr. Food Res., 2009, 53, 897-903.
240. Han, J.; Talorete, T. P. N.; Yamada, P.; Isoda, H. Antiproliferative and apoptotic effects of oleuropein and hydroxytyrosol on human breast cancer MCF-7 cells. Cytotechnol., 2009, 59, 45-53.
241. Granados-Principal, S.; Quiles, J. L.; Ramirez-Tortosa, C.; Camacho-Corencia, P.; Sanchez-Rovira, P.; Vera-Ramirez, L.; Ramirez-Tortosa, M. C. Hydroxytyrosol inhibits growth and cell proliferation and promotes high expression of sfrp4 in rat mammary tumours. Mol. Nutr. Food Res., 2011, 55 (Suppl. 1), S117-S126.
242. Bernini, R.; Mincione, E.; Crisante, F.; Barontini, M.; Fabrizi, G.; Gentili, P. Chemoselective and efficient carboxymethylation of the alcoholic chain of phenols by dimethyl carbonate (DMC). Tetrahedron Lett., 2007, 48, 7000-7003.
243. Bernini, R.; Mincione, E.; Barontini, M.; Crisante, F. Convenient synthesis of hydroxytyrosol and its lipophilic derivatives from tyrosol or homovanillyl alcohol. J. Agric. Food Chem., 2008, 56, 8897-8904.
244. Bernini, R.; Mincione, E.; Barontini, M.; Crisante, F. Procedimento per la preparazione di derivati dell'idrossitirosolo e di idrossitirosolo via demetilazione ossidativa. IT Patent 0001382586, December 22, 2010.
245. Bernini, R.; Mincione, E.; Crisante, F.; Barontini, M.; Fabrizi, G. A novel use of the recyclable polymer-supported IBX: an efficient chemoselective and regioselective oxidation of phenolic compounds. The case of hydroxytyrosol derivatives. Tetrahedron Lett., 2009, 50, 1307-1310.
246. Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. Lebensm.-Wiss. u.-Technol., 1995, 28, 25-30.
247. Bernini, R.; Cacchi, S.; Fabrizi, G.; Filisti, E. 2-Arylhydroxytyrosol derivatives via Suzuki-Miyaura cross-coupling. Org. Lett., 2008, 10, 3457-3460.
248. Trujillo, M.; Mateos, R.; Collantes De Teran, L.; Espartero, J. L.; Cert, R.; Jover, M.; Alcudia, F.; Bautista, J.; Cert, A.; Parrado, J. Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. J. Agric. Food Chem., 2006, 54, 3779-3785
249. Grasso, S.; Siracusa, L.; Spatafora, C.; Renis, M.; Tringali, C. Hydroxytyrosol lipophilic analogues: Enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection. Bioorg. Chem., 2007, 35, 137-152.
250. Piacente, S.; Pizza, C.; De Tommasi, N.; Mahmood, N. Constituents of Ardisia japonica and their in vitro anti-HIV activity. J. Nat. Prod., 1996, 59, 565-569.
251. Bernini, R.; Barontini, M.; Mosesso, P.; Pepe, G.; Willför, S. M.; Sjöholm, R. E.; Eklund, P.; Saladino, R. A selective de-O-methylation of guaiacyl lignans to corresponding catechol derivatives by 2-iodoxybenzoic acid (IBX). The role of the catechol moiety on the toxicity of lignans. Org. Biomol. Chem., 2009, 7, 2367-2377.
252. Huang, Y.; Zhang, J.; Pettus, T. R. R. Synthesis of (±)-brazilin using IBX. Org. Lett., 2005, 7, 5841-5844.
253. Livingstone, R. Anthocyanins, brazilin, and related compounds. Nat. Prod. Rep., 1987, 4, 25-33.
254. Tolman, R.L.; Chin, A.C. WO Patent 0193864, December 13, 2001.
255. Mar, W.; Lee, H.-T.; Je, K.-H.; Choi, H.-Y.; Seo, E.-K. A DNA strandnicking principle of a higher plant, Caesalpinia sappan. Arch. Pharm. Res., 2003, 26, 147-150.
256. Nilsson, J. Lars G.; Selander, H.; Sievertsson, H.; Skånberg, I.; Svensson, K.-G. Directive effects in the bromination of bicyclic phenols. Acta Chem. Scand., 1971, 25, 94-100.
257. Lange, J.; Hoogeveen, S.; Veerman, W.; Wals, H. Regioselective aminomethylations of bicyclic phenols. Heterocycles, 2000, 53, 197-204.
258. Selenski, C.; Pettus, T. R. R. (±)-Diinsininone: made nature's way. Tetrahedron, 2006, 62, 5298-5307.
259. Deffieux, D.; Gaudrel-Grosay, S.; Grelard, A.; Chalumeau, C.; Quideau, S. Stable solid-supported leucoanthocyanidin variants for flavanoid biosynthesis elucidation. Tetrahedron Lett., 2009, 50, 6567-6571.
260. Chalumeau, C. Développement d'Outils Chimiques pour l'Elucidation de la Biosynthèse des Flavonoïdes du Raisin: Anthocyanes versus Proanthocyanidines. PhD Thesis, Université Bordeaux 1: France, December 2010, Order No. 4188.
261. Chalumeau, C.; Deffieux, D.; Chaignepain, S.; Quideau, S. Development of an Affinity-Based Proteomic Strategy for the Elucidation of Proanthocyanidin Biosynthesis. ChemBioChem, 2011, 12, 1193-1197.
262. Barontini, M.; Bernini, R.; Crisante, F.; Fabrizi, G. Selective and efficient modifications of flavonoids with 2-iodoxybenzoic acid (IBX). Tetrahedron, 2010, 66, 6047-6053.
263. Zhang, Yu. Ab initio study on the anti-HIV activities of hydroxyflavones. Jiegou Huaxue, 2005, 24, 462-466.
264. Dewar, M. J. S. A theoretical discussion of o:p ratios and orientation in benzene substitution. J. Chem. Soc., 1949, 463-468.
265. Nilsson, J. Lars, G.; Sievertsson, H.; Selander, H. On the preferential oxidative coupling at the 5- versus the 7-position in tocopherols and related 6- chromanols. Acta Chem. Scand., 1969, 23, 859-870.
266. Van Zanden, J. J.; Wortelboer, H. M.; Bijlsma, S.; Punt, A.; Usta, M.; Van Bladeren P. J.; Rietjens, I. M. C. M.; Cnubben, N. H. P. Quantitative structure activity relationship studies on the flavonoids mediated inhibition of multidrug resistance proteins 1 and 2. Biochem. Pharm., 2005, 69, 699-708.
267. Taleb-Contini, S. H.; Kanashiro, A.; Kabeya, L. M.; Polizello, A. C. M.; Lucisano-Valim, Y. M.; Oliveira, D. C. R. Immunomodulatory effects of methoxylated flavonoids from two Chromolaena species: structure-activity relationships. Phytotherapy Res., 2006, 20, 573-575.
268. Tsuji, P. A.; Walle, T. Inhibition of benzo[a]pyrene-activating enzymes and DNA binding inhuman bronchi al epithelial BEAS-2B cells by methoxylated flavonoids. Carcinogenesis, 2006, 27, 1579-1585.
269. Wen, X.; Walle, T. Methylated flavonoids have greatly improved intestinal adsorption and metabolic stability. Drug Metab. Dispos., 2006, 34, 1786-1792.
270. Walle, T.; Ta, N.; Kawamori, T.; Wen, X.; Tsuji, P.A.; Walle. U. K. Cancer chemopreventive properties of orally bioavailable flavonoids -methylated versus unmethylated flavones. Biochem. Pharm., 2007, 73, 1288-1296.
271. Cavalieri, E.; Rogan, E.; Chakravarti, D. The role of endogenous catechol quinines in the initiation of cancer and neurodegenerative diseases. Methods Enzymol., 2004, 382, 293-319.
272. Lippert, T. H.; Seeger, H.; Mueck, A. O. The impact of endogenous estradiol metabolites on carcinogenesis. Steroids, 2000, 65, 357-369.
273. Saeed, M.; Zahid, M.; Rogan, E.; Cavalieri, E. Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent. Steroids, 2005, 70, 173-178.
274. Pezzella, A.; Lista, L.; Napolitano, A.; d'Ischia, M. An expedient one-pot entry to catecholestrogens and other catechol compounds via IBX-mediated phenolic oxygenation. Tetrahedron Lett., 2005, 46, 3541-3544.
275. Bernini, R.; Mincione, E.; Barontini, M.; Crisante, F. Procedimento per la preparazione di derivati dell'idrossitirosolo e di idrossitirosolo. IT Patent 0001381959, September 27, 2010.
276. Bernini, R.; Crisante, F.; Merendino, N.; Molinari, R.; Soldatelli, M. C.; Velotti, F. Synthesis of a novel ester of hydroxytyrosol and α-lipoic acid exhibiting an antiproliferative effect on human colon cancer HT-29 cells. Eur. J. Med. Chem., 2011, 46, 439-446.
277. Bernini, R.; Crisante, F.; Barontini, M., Fabrizi, G. A new and efficient route for the synthesis of naturally occurring catecholamines. Synthesis, 2009, 22, 3838-3842.
278. Hoffmann, B. B.; Lefkowitz, R. J. In: The Pharmacological Basis of Therapeutics (9th Edition); Hardman, J. G., Limbird, L. E., Molinoff, P. B., Ruddon, R. W., Gilman, A. F., Eds.; McGraw-Hill, New York, 1996; 199-248.
279. Bernini, R.; Barontini,M.; Crisante, F.; Ginnasi, M. C.; Saladino, R. A novel and efficient synthesis of DOPA and DOPA peptides by oxidation of tyrosine residue with IBX. Tetrahedron Lett., 2009, 50, 6519-6521.
280. Liu, Z.; Hu, Bi-H.; Messersmith, P. B. Convenient synthesis of acetonideprotected 3,4-dihydroxyphenylalanine (DOPA) for Fmoc solid-phase peptide synthesis. Tetrahedron Lett., 2008, 49, 5519-5521, and references cited therein.
281. Bernini, R.; Barontini, M.; Spatafora, C. New lipophilic piceatannol derivatives exhibiting antioxidant activity prepared by aromatic hydroxylation with 2-iodoxybenzoic acid (IBX). Molecules, 2009, 14, 4669-4681.
282. Tada, M.; Ohkanda, T.; Kurabe, J. Syntheses of carnosic acid and carnosol, anti-oxidants in rosemary, from pisiferic acid, the major constituent of sawara. Chem. Pharm. Bull., 2010, 58, 27-29.