Chemical and electrochemical oxidative activation of arenol derivatives for carbon-carbon bond formation

Current Organic Chemistry

Volumn 8, Issue 2, 2004, Pages 113-148

  Quideau, S ^a,b   Pouysegu L ^a,b   Deffieux, D ^a,b  

^a INSTITUT EUROPÉEN DE CHIMIE ET BIOLOGIE   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CARBON; CHEMICAL BONDS; ETHERS; OXIDATION; REACTION INTERMEDIATES;

ALKYL ETHERS; AROMATIC RINGS; BOND FORMATION; CARBON-CARBON BOND FORMATION; ELECTROCHEMICALS; FUNCTIONALIZATIONS; OXIDATION PROCESS; SIMPLE++; SPECIFIC BONDS; TWO-ELECTRON OXIDATION PROCESS;

CHEMICAL ACTIVATION;

ALKYL ETHER; ALKYL GROUP; AROMATIC COMPOUND; CARBON; CATION; DISCORHABDIN C; ION; ISOBOLDINE; MICHELLAMINE A; MICHELLAMINE B; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PRIANOSIN A; RETICULINE;

BIOCHEMISTRY; CHEMICAL BOND; CHEMICAL REACTION; CHEMISTRY; CYCLOADDITION; ELECTROCHEMICAL ANALYSIS; ELECTRON; HYDROXYLATION; MICHAEL ADDITION; MOLECULE; OXIDATION; OXYGENATION; REVIEW; SYNTHESIS;

EID: 0346496337     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043486016     Document Type: Review

References (269)

1. Quideau, S.; Feldman, K. S. Tetrahedron Symposium-in-Print 2001, 57, ix-x, and articles cited therein.
2. Quideau, S. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002, pp. 539-573.
3. Yamamura, S.; Nishiyama, S. Synlett 2002, 533-543.
4. Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327-415.
5. Morrow, G. W. In Organic Electrochemistry; Lund, H., Baizer, M. M., Eds.; Marcel Decker: New York 2000, pp. 589-620.
6. Quideau, S.; Pouységu, L. Org. Prep. Proc. Int. 1999, 31, 617-680, and reference cited therein.
7. Yamamura, S. In New Challenges in Organic Electrochemistry; Osa, T., Ed.; Gordon and Breach Science Publishers: Amsterdam, 1998, pp. 166-181.
8. Whiting, D. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp. 659-703, and references cited therein.
9. Rieker, A.; Beisswenger, R.; Regier, K. Tetrahedron 1991, 47, 645-654.
10. Eickhoff, H.; Jung, G.; Rieker, A. Tetrahedron 2001, 57, 353-364, and reference cited therein.
11. Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273-282.
12. Waters, W. A. J. Chem. Soc. (B) 1971, 2026-2029.
13. Abramovitch, R. A.; Alvernhe, G.; Bartnik, R.; Dassanayake, N. L.; Inbasekaran, M. N.; Kato, S. J. Am. Chem. Soc. 1981, 103, 4558-4565.
14. Fürstner, A.; Stelzer, F.; Rumbo, A.; Krause, H. Chem. Eur. J. 2002, 8, 1856-1871.
15. Syrjänen, K.; Brunowo, G. Tetrahedron 2001, 57, 365-370, and references cited therein.
16. Quideau, S.; Feldman, K. S. Chem. Rev. 1996, 96, 475-503.
17. Haslam, E.; Cai, Y. Nat. Prod. Rep. 1994, 41-66.
18. McDonald, P. D.; Hamiltoon, G. A. In Oxidation in Organic Chemistry, Part B; Trahanovsky, W. S., Ed.; Academic Press: New York, 1973, pp. 97-134.
19. Kametani, T.; Fukumoto, K. Synthesis 1972, 657-674.
20. Oxidative Coupling of Phenols, Taylor, W. I., Battersby, A. R., Eds; Marcel Dekker, Inc.: New York, 1967; Vol. 1.
21. Musso, H. Angew. Chem., Int. Ed. Engl. 1963, 2, 723-735.
22. Barton, D. H. R. Proc. Chem. Soc. 1963, 293-298.
23. Whalley, W. B. In Recent Developments in The Chemistry of Natural Phenolic Compounds; Ollis, W. D., Ed.; Pergamon Press: New York, 1961, pp. 20-58.
24. Armstrong, D. R.; Cameron, C.; Nonhebel, D. C.; Perkins, P. G. J. Chem. Soc., Perkin Trans. 2 1983, 587-589, and other papers in the same series.
25. Hovorka, M.; Günterova, J.; Zavada, J. Tetrahedron Lett. 1990, 31, 413-416.
26. Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891-1896, and references cited therein.
27. Swenton, J. S. Acc. Chem. Res. 1983, 16, 74-81.
28. Swenton, J. S. In The Chemistry of Quinonoid Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley: New York, 1988; Vol. 2, Part 2, pp. 899-962.
29. Pelter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677-680.
30. Deffieux, D.; Fabre, I.; Courseille, C.; Quideau S. J. Org. Chem. 2002, 67, 4458-4465.
31. Weinberg, N. L.; Belleau, B. Tetrahedron 1973, 29, 279-285.
32. Belleau, B.; Weinberg, N. L. J. Am. Chem. Soc. 1963, 85, 2525-2526.
33. Ronlán, A.; Bechgaard, K.; Parker, V. D. Acta Chem. Scand. 1973, 27, 2375-2382.
34. Bechgaard, K.; Hammerich, O.; Moe, N. S.; Ronlán A.; Svanholm, U.; Parker, V. D. Tetrahedron Lett. 1972, 13, 2271-2274.
35. Hammerich, O.; Moe, N. S.; Parker, V. D. J. Chem. Soc., Chem. Commun. 1972, 156-157.
36. Svanholm, U.; Parker, V. D. Tetrahedron Lett. 1972, 13, 471-472.
37. Bringmann, G.; Tasler, S. Tetrahedron 2001, 57, 331-343.
38. Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991.
39. Tohma, H.; Morioka, H.; Takizawa, S.; Arisawa, M.; Kita, Y. Tetrahedron 2001, 57, 345-352.
40. Takada, T.; Arisawa, M.; Gyoten, M.; Hamada, R.; Tohma, H.; Kita, Y. J. Org. Chem. 1998, 63, 7698-7706.
41. Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 116, 3357-3366.
42. Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1993, 115, 1162-1163.
43. Nelson, T. D.; Meyers, A. I. Tetrahedron Lett. 1993, 34, 3061-3062, and references cited therein.
44. Sainsbury, M. Tetrahedron 1980, 36, 3327-3359, and references cited therein.
45. McKillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504-6512, and references cited therein.
46. Lessene, G.; Feldman, K. S. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, 2002, pp. 479-538.
47. Adam, H.; Khanbabaee, K.; Krohn, K.; Küpke, J.; Rieger, H.; Steingröver, K.; Vinke, I. In Peroxide Chemistry, Mechanistic and Preparative Aspects of Oxygen Transfer; W., Ed.; Wiley-VCH; Weinheim, 2000, pp. 469-493.
48. Akai, S.; Kita, Y. Org Prep. Proc. Int. 1998, 30, 605-629.
49. Bacon, R.G.R.; Izzat, A.R. J. Chem. Soc. (C) 1966, 791-793.
50. McKillop, A.; Perry, D. H.; Edwards, M.; Antus, S.; Farkas, L.; Nógrádi, M.; Taylor, E. C. J. Org. Chem. 1976, 41, 282-287.
51. Wessely, F.; Lauterbach-Keil, G.; Sinwel, F. Monatsh. Chem. 1950, 81, 811-818.
52. Bubb, W. A.; Sternhell, S. Tetrahedron Lett. 1970, 51, 4499-4502.
53. Hewitt, D. G. J. Chem. Soc. (C) 1971, 2967-2973.
54. Forrester, A. R.; Thomson, R. H.; Woo, S.-J. J. Chem. Soc., Perkin Trans. 1 1975, 2340-2348.
55. Mandal, S.; Macikenas, D.; Protasiewicz, J. D.; Sayre, L. M. J. Org. Chem. 2000, 65, 4804-4809.
56. Sharma, M.; Jain, R. Chem.-Biol. Interactions 1998, 108, 171-185.
57. Ma, Y.-A.; Guo, Z.-W.; Sih, C. J. Tetrahedron Lett. 1998, 39, 9357-9360.
58. Guo, Z.-W.; Salamonczyk, G. M.; Han, K.; Machiya, K.; Sih, C. J. J. Org. Chem. 1997, 62, 6700-6701.
59. Michon, T.; Chenu, M.; Kellershon, N.; Desmadril, M,; Guéguen, J. Biochemistry 1997, 36, 8504-8513.
60. Chabanet, A.; Goldberg, R.; Catesson, A.-M.; Quinet-Szély, M.; Delaunay, A.-M.; Faye, L. Plant Physiol. 1994, 106, 1095-1102.
61. Bauer, W.; Stadler, R.; Zenk, M. H. Bot. Acta 1992, 105, 370-374.
62. Peter M. G. Angew. Chem., Int. Ed. Engl. 1989, 28, 555-570.
63. Mayer, A. M. Phytochemistry 1987, 26, 11-20.
64. Kametani, T.; Nemoto, H.; Kobari, T.; Takano, S. J. Heterocycl. Chem. 1970, 7, 181-186.
65. Brown, B. R. In Oxidative Coupling of Phenols; Taylor, W. I., Battersby, A. R. Eds.; Marcel Dekker Inc.: New York, 1967, pp. 167-201.
66. Gross, A. J.; Sizer I. W. J. Biol. Chem. 1959, 234, 1611-1614.
67. Stadler, R.; Zenk, M. H. J. Biol. Chem. 1993, 268, 823-831.
68. Gerardy, R.; Zenk, M. H. Phytochemistry 1993, 32, 79-86.
69. Chioccara, F.; Poli, S.; Rindone, B.; Pilati, T.; Brunow, G.; Pietikäinen, P.; Setälä, H. Acta Chem. Scand. 1993, 47, 610-616.
70. Bozell, J. J.; Hames, B. R.; Dimmel, D. R. J. Org. Chem. 1995, 60, 2398-2404.
71. Nishinaga, A.; Shimizu, T.; Toyoda, Y.; Matsuura, T.; Hirotsu, K. J. Org. Chem. 1982, 47, 2278-2285.
72. Nishinaga, A.; Tomita, H.; Nishizawa, K.; Matsuura, T.; Ooi, S.; Hirotsu, K. J. Chem. Soc., Dalton 1981, 1504-1514.
73. Higuchi, T.; Satake, C.; Hirobe, M. J. Am. Chem. Soc. 1995, 117, 8879-8880.
74. Schwartz, M. A.; Rose, B. F.; Holton, R. A.; Scott, S. W.; Vishnuvajjala, B. J. Am. Chem. Soc. 1977, 99, 2571-2578.
75. Smith, P. L.; Chordia, M. D.; Harman, W. D. Tetrahedron 2001, 57, 8203-8225.
76. Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917-2940.
77. Pike, R. D., Sweigart, D. A. Synlett 1990, 565-571.
78. Pearson, A. J.; Gontcharov, A. V. J. Org. Chem. 1998, 63, 152-162.
79. Pearson, A. J.; Zhu, P. Z. J. Am. Chem. Soc. 1993, 115, 10376-10377.
80. Astruc, D. Synlett 1991, 369-380.
81. Kane-Maguire, L. A. P.; Honig, E. D.; Sweigart, D. A. Chem. Rev. 1984, 84, 525-543.
82. Amouri, H.; Le Bras, J. Acc. Chem. Res. 2002, 35, 501-510.
83. Amouri, H.; Le Bras, J.; Vaissermann, J. Organometallics 1998, 17, 5850-5857.
84. Feldman, K. S.; Quideau, S.; Appel, H. M. J. Org. Chem. 1996, 61, 6656-6665.
85. Quideau, S.; Feldman, K. S.; Appel, H. M. J. Org. Chem. 1995, 60, 4982-4983.
86. Horner, L.; Teichmann, K.-H.; Weber, K.-H.; Geyer, E. Chem. Ber. 1965, 98, 1233-1246.
87. Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208.
88. Chiba, K.; Arakawa, T.; Tada, M. Chem. Commun. 1996, 1763-1764.
89. Bolton, J. L.; Trush, M. A.; Penning, T. M.; Dryhurst, G.; Monks, T. J. Chem. Res. Toxicol. 2000, 13, 135-160.
90. Angle, S. R.; Arnaiz, D. O.; Boyce, J. P.; Frutos, R. P.; Louie, M. S.; Mattson-Arnaiz, H.; Rainier, J. D.; Turnbull, K. D.; Yang, W. J. Org. Chem. 1994, 59, 6322-6337.
91. Thompson, D. C.; Thompson, J. A.; Sugumaran, M.; Moldéus, P. Chem.-Biol. Interactions 1992, 86, 129-162.
92. Kutyrev, A. A. Tetrahedron 1991, 47, 8043-8065.
93. Wanzlick, H. W.; Lehmann-Horchler, M.; Mohrmann, S.; Gritzky, R.; Heidepriem, H.; Pankow, B. Angew. Chem., Int. Ed. Engl. 1964, 3, 401-408, and references cited therein.
94. Ognyanov, V. I.; Petrov, O. S.; Tiholov, E. P.; Mollov, N. M. Helv. Chim. Acta 1989, 72, 353-360.
95. Pouységu, L.; Avellan, A.-V.; Quideau, S. J. Org. Chem. 2002, 67, 3425-3436.
96. Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856-866.
97. Quideau, S.; Pouységu, L.; Oxoby, M.; Looney, M. A. Tetrahedron 2001, 57, 319-329.
98. Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego 1997.
99. Varvoglis, A. Tetrahedron 1997, 53, 1179-1255.
100. Tamura, Y.; Yakura, T.; Haruta, J.-i.; Kita, Y. J. Org. Chem. 1987, 52, 3927-3930.
101. Siegel, A.; Antony, F. Monatsh. Chem. 1955, 86, 292-300.
102. Kida, M.; Sueda, T.; Goto, S.; Okuyama, T.; Ochiai, M. Chem. Commun. 1996, 1933-1934.
103. Kürti, L.; Herczegh, P.; Visy, J.; Simonyi, M.; Antus, S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1999, 379-380.
104. Barton, D. H. R.; Yadav-Bhatnagar, N.; Finet, J.-P.; Khamsi, J.; Motherwell, W. B.; Stanforth, S. P. Tetrahedron 1987, 43, 323-332.
105. Fatiadi, A. J. Synthesis 1974, 229-272.
106. Kita, Y.; Egi, M.; Takada, T.; Tohma, H. Synthesis 1999, 885-897.
107. Kita, Y.; Takada, T.; Tohma, H. Pure Appl. Chem. 1996, 68, 627-630.
108. Moreno, I.; Tellitu, I.; Herrero, M. T.; SanMartín, R.; Domínguez, E. Curr. Org. Chem. 2002, 6, 1433-1452.
109. Moeller, K. D. Tetrahedron 2000, 56, 9527-9554.
110. Hammerich, O.; Svenmark, B. In Organic Electrochemistry; Lund, H., Baizer, M. M., Eds.; Marcel Decker: New York, Basel, Hong Kong, 1991, pp. 615-657.
111. Fry, A. J. Synthetic Organic Electrochemistry, 2nd ed.; Wiley: New York, 1989.
112. Schäfer, H.-J. Angew. Chem., Int. Ed. Engl. 1981, 20, 911-934.
113. Baizer, M. M.; Lund, H. Organic Electrochemistry. An Introduction and a Guide; Marcel Decker: New York, 2000.
114. Nishiyama, A.; Eto, H.; Terada, Y.; Iguchi, M.; Yamamura, S. Chem. Pharm. Bull. 1983, 31, 2820-2833.
115. Iguchi, M.; Nishiyama, A.; Terada, Y.; Yamamura, S. Chem. Lett. 1978, 451-454.
116. Yoshida, J.-I.; Suga, S.; Suzuki, S.; Kinomura, N.; Yamamoto, A.; Fujiwara, K. J. Am. Chem. Soc. 1999, 121, 9546-9549.
117. Yoshida, J.; Sugawara, M.; Tatsumi, M.; Kise, N. J. Org. Chem. 1998, 63, 5950-5961.
118. Chiba, T.; Yoshiyuki, T. J. Org. Chem. 1977, 42, 2973-2977.
119. Ponsold, K.; Kasch, H. Tetrahedron Lett. 1979, 46, 4465-4466.
120. Andreades, S.; Zahnow E. W. J. Am. Chem. Soc. 1969, 91, 4181-4190.
121. Anderson, R. A.; Dalgleish, D. T.; Nonhebel, D. C.; Pauson, P. L. J. Chem. Res. (S) 1977, 12-13.
122. Chen, C.-L.; Connors, W. J.; Shinker, W. M. J. Org. Chem. 1969, 34, 2966-2971.
123. Quideau, S.; Ralph, J. Holzforschung 1994, 48, 12-22.
124. Ralph, J.; Helm, R. F.; Quideau, S. J. Chem. Soc., Perkin Trans. 1 1992, 2971-2980.
125. Hapiot, P.; Pinson, J.; Neta, P.; Francesch, C.; Mhamdi, F.; Rolando, C.; Schneider, S. Phytochemistry 1994, 36, 1013-1020.
126. Orlandi, M.; Rindone, B.; Molteni, G.; Rummakko, P.; Brunow, G. Tetrahedron 2001, 57, 371-378.
127. Quideau, S.; Ralph, J. J. Chem. Soc., Perkin Trans. 1 1997, 2351-2358.
128. Baumgartner, J.; Neukom, H. Chimia 1972, 26, 366-368.
129. Bringmann, G.; Vitt, D. J. Org. Chem. 1995, 60, 7674-7681.
130. Prelog, V.; Helmchen, G. Angew. Chem., Int. Ed. Engl. 1982, 21, 567-583.
131. Bringmann, G.; Götz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090-1097.
132. Bringmann, G.; Götz, R.; Harmsen, S.; Holenz, J.; Walter, R. Liebigs Ann. 1996, 2045-2058.
133. Bringmann, G.; Harmsen, S.; Holenz, J.; Geuder, T.; Götz, R.; Keller, P. A.; Walter, R.; Hallock, Y. F.; Cardellina II, J. H.; Boyd, M. R. Tetrahedron 1994, 50, 9643-9648.
134. Schlauer, J.;Rückert, M.; Wiesen, B.; Herderich, M.; Aké Assi, L.; Haller, R. D.; Bär, S.; Fröhlich, K.-U.; Bringmann, G. Arch. Biochem. Biophys. 1998, 350, 87-94.
135. Bringmann, G.; Saeb, W.; Mies, J.; Messer, K.; Wohlfarth, M.; Brun, R. Synthesis 2000, 1843-1847.
136. Bringmann, G.; Pabst, T.; Rycroft, D. S.; Connolly, J. D. Tetrahedron Lett. 1999, 40, 483-486.
137. Bringmann, G.; Pabst, T.; Busemann, S.; Peters, K.; Peters, E.-M. Tetrahedron 1998, 54, 1425-1438.
138. Lin, G.; Zhang, A. Tetrahedron Lett. 1999, 40, 341-344.
139. Bringmann, G.; Ledermann, A.; Stahl, M.; Gulden, K.-P. Tetrahedron 1995, 51, 9353-9360.
140. Bringmann, G.; Ledermann, A.; François, G. Heterocycles 1995, 40, 293-300.
141. Ito, C.; Thoyama, Y.; Omura, M.; Kajiura, I.; Furukawa, H. Chem. Pharm. Bull. 1993, 41, 2096-2100.
142. Johnston, K. M. Tetrahedron Lett. 1967, 8, 837-839.
143. Nishiyama, S.; Kim, M. H.; Yamamura, S. Tetrahedron Lett. 1994, 35, 8397-8400.
144. Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1983, 24, 5011-5012.
145. Shizuri, Y.; Nakamura, K.; Yamamura, S. J. Chem. Soc., Chem. Commun. 1985, 530-531.
146. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135-2143.
147. El-Seedi, H. R.; Yamamura, S.; Nishiyama, S. Tetrahedron Lett. 2002, 43, 3301-3304.
148. Kerns, M. L.; Conroy, S. M.; Swenton, J. S. Tetrahedron Lett. 1994, 35, 7529-7532.
149. Chiba, K.; Fukuda, M.; Kim, S.; Kitano, Y.; Tada, M. J. Org. Chem. 1999, 64, 7654-7656.
150. Carlini, R.; Higgs, K.; Taylor, N.; Rodrigo, R. Can. J. Chem. 1997, 75, 805-816.
151. Carlini, R.; Fan, C.-L.; Herrington, D.; Higgs, K.; Rodrigo, R.; Taylor, N. Aust. J. Chem. 1997, 50, 271-278.
152. Chiba, K.; Tada, M. J. Chem. Soc., Chem. Commun. 1994, 2485-2486.
153. Lee, J.; Snyder, J. K. J. Org. Chem. 1990, 55, 4995-5008.
154. Grundmann, C. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Bayers, O., Eds.; Thieme: Stuttgart, 1979; Vol Bd. VII/3b, pp. 3-185.
155. Horspool, W. M.; Tedder, J. M.; Din, Z. U. J. Chem. Soc. (C) 19721, 1638-1640, and other papers in the same series.
156. Liao, C.-C. In Modern Methodology in Organic Synthesis; Shono, T., Ed.; Kodansha: Tokyo, 1992, pp. 409-424.
157. Souza, F. E. S.; Rodrigo, R. Chem. Commun. 1999, 1947-1948.
158. Nicolaou, K. C.; Vassilikogiannakis, G.; Simonsen, K. B.; Baran, P. S.; Zhong, Y.-L.; Vidali, V. P.; Pitsinos, E. N.; Couladouros, E. A. J. Am. Chem. Soc. 2000, 122, 3071-3079.
159. Barnes-Seeman, D.; Corey, E. J. Org. Lett. 1999, 1, 1503-1504.
160. Golabi, S. M.; Nematollahi, D. J. Electroanal. Chem. 1997, 420, 127-134.
161. Nematollahi, D.; Forooghi, Z. Tetrahedron 2002, 58, 4949-4953.
162. Grujic, Z.; Tabakovic, I.; Trkovnik, M. Tetrahedron Lett. 1976, 52, 4823-4824.
163. Tabakovic, I.; Grujic, Z.; Bejtovic, Z. J. Heterocycl. Chem. 1983, 20, 635-638.
164. Quideau, S.; Feldman, K. S. J. Org. Chem. 1997, 62, 8809-8813.
165. Speiser, B. Doctoral Thesis, University of Tübingen, 1981.
166. Quideau, S.; Looney, M. A.; Pouységu, L. Org. Lett. 1999, 1, 1651-1654.
167. Palmquist, U.; Ronlan, A.; Parker, V. D. Acta Chem. Scand. 1974, B 28, 267-269.
168. Swenton, J. S.; Carpenter, K.; Chen, Y.; Kerns, M. L.; Morrow, G. W. J. Org. Chem. 1993, 58, 3308-3316.
169. Callinan, A.; Chen, Y.; Morrow, G. W.; Swenton, J. S. Tetrahedron Lett. 1990, 31, 4551-4552.
170. Morrow, G. W.; Chen, Y.; Swenton, J. S. Tetrahedron 1991, 47, 655-664.
171. Morrow, G. W.; Swenton, J. S. Tetrahedron Lett. 1987, 28, 5445-5448.
172. Rama Krishna, K. V.; Sujatha, K.; Kapil, R. S. Tetrahedron Lett. 1990, 31, 1351-1352.
173. Swenton, J. S.; Callinan, A.; Chen, Y.; Rohde, J. J.; Kerns, M. L.; Morrow, G. W. J. Org. Chem. 1996, 61, 1267-1274.
174. Tao, X. L.; Cheng, J. F.; Nishiyama, A.; Yamamura, S. Tetrahedron 1994, 50, 2017-2028.
175. Cheng, J. F.; Nishiyama, S.; Yamamura, S. Chem. Lett. 1990, 1591-1594.
176. Tohma, H.; Harayama, Y.; Hashizume, M.; Iwata, M.; Egi, M.; Kita, Y. Angew. Chem., Int. Ed. Engl. 2002, 41, 348-350.
177. Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857-5864.
178. Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamanda, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625-6633.
179. Eichhorn, J.; Takada, T.; Kita, Y.; Zenk, M. H. Phytochemistry 1998, 49, 1037-1047.
180. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
181. Nabana, T.; Togo, H. J. Org. Chem. 2002, 67, 4362-4365.
182. Ley, S. V.; Thomas, A. W.; Finch, H. J. Chem. Soc., Perkin Trans. 1 1999, 669-671.
183. Togo, H.; Abe, S.; Nogami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1999, 72, 2351-2356.
184. Togo, H.; Nogami, G.; Yokoyama, M. Synlett 1998, 534-536.
185. Zupan, M. Collect. Czech., Chem. Commun. 1977, 42, 266-274.
186. Zupan, M.; Pollak, A. J. Chem. Soc., Chem. Commun. 1975, 715-716.
187. Yamada, Y.; Okawara, M. Makromol. Chem. 1972, 152, 153-162.
188. Ley, S. V.; Baxendale, I. R.; Brusotti, G.; Caldarelli, M.; Massi, A.; Nesi, M. Il Farmaco 2002, 57, 321-330.
189. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
190. Ley, S. V.; Schucht, O.; Thomas, A. W.; Murray, P. J. J. Chem. Soc., Perkin Trans. 1 1999, 1251-1252.
191. Baxendale, I. R.; Ley, S. V.; Piutti, C. Angew. Chem., Int. Ed. Engl. 2002, 41, 2194-2197.
192. Barton, D. H. R.; Bhakuni, D. S.; James, R.; Kirby, G. W. J. Chem. Soc. (C) 1967, 128-132.
193. White, J. D.; Caravatti, G.; Kline, T. B.; Edstrom, E. Tetrahedron 1983, 39, 2393-2397.
194. Szantay, C.; Blasko, G.; Barczai-Beke, M. Tetrahedron Lett. 1980, 21, 3509-3512.
195. Schwartz, M. A.; Mami, I. S. J. Am. Chem. Soc. 1975, 97, 1239-1240.
196. Burnett, D. A.; Hart, D. J. J. Org. Chem. 1987, 52, 5662-5667.
197. Schwartz, M. A.; Vanderlaan, D. G. J. Org. Chem. 1985, 50, 743-747.
198. Szantay, C.; Barczai-Beke, M.; Péchy, P.; Blasko, G.; Dörnyei, G. J. Org. Chem. 1982, 47, 594-596.
199. Schwartz, M. A.; Pham, P. T. K. J. Org. Chem. 1988, 53, 2318-2322.
200. Hoshino, O.; Suzuki, M.; Ogasawara, H. Tetrahedron 2001, 57, 265-271, and references cited therein.
201. Umezawa, B.; Hoshino, O. Heterocycles 1975, 3, 1005-1033.
202. Hoshino, O.; Suzuki, M.; Ogasawara, H. Heterocycles 2000, 52, 751-760.
203. Hoshino, O.; Ogasawara, H.; Suzuki, M. Heterocycles 1990, 30, 385-388.
204. Hoshino, O.; Ogasawara, H.; Suzuki, M.; Umezawa, B. Heterocycles 1987, 25, 151-153.
205. Ward, R. S.; Pelter, A.; Abd-El-Ghani, A. Tetrahedron 1996, 52, 1303-1336.
206. Pelter, A.; Ward, R. S.; Abd-El-Ghani, A. J. Chem. Soc., Perkin Trans. 1 1992, 2249-2251.
207. Pelter, A.; Ward, R. S.; Abd-El-Ghani, A. Tetrahedron: Asymmetry 1994, 5, 329-332.
208. Robin, J.-P.; Landais, Y. Tetrahedron 1992, 48, 819-830.
209. Tanaka, M.; Mitsuhashi, H.; Wakamatsu, T. Tetrahedron Lett. 1992, 33, 4161-4164.
210. Khanbabaee, K.; Van Ree, T. Synthesis 2001, 1585-1610.
211. Feldman, K. S.; Sahasrabudhe, K.; Quideau, S.; Hunter, K. L.; Lawlor, M. D. In Plant Polyphenols 2: Chemistry, Biology, Pharmacology, Ecology; Gross, G. G., Hemingway, R. W., Yoshida, T., Eds.; Kluwer Academic/Plenum Publishers: New York, NY, 1999; Vol. Basic Life Science 66, pp. 101-125.
212. Feldman, K. S.; Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc. 1994, 116, 1742-1745.
213. Feldman, K. S.; Sambandam, A. J. Org. Chem. 1995, 60, 8171-8178.
214. Feldman, K. S.; Smith, R. S. J. Org. Chem. 1996, 61, 2606-2612.
215. Feldman, K. S.; Lawlor, M. D. J. Am. Chem. Soc. 2000, 122, 7396-7397.
216. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2001, 123, 4475-4479.
217. Maki, S.; Kosemura, S.; Yamamura, S.; Ohba, S. Tetrahedron Lett. 1993, 34, 6083-6086.
218. Maki, S.; Toyoda, K.; Mori, T.; Kosemura, S.; Yamamura, S. Tetrahedron Lett. 1994, 35, 4817-4818.
219. Harada, Y.; Maki, S.; Niwa, H.; Hirano, T.; Yamamura, S. Synlett 1998, 1313-1314.
220. Maki, S.; Toyoda, K.; Kosemura, S.; Yamamura, S. Chem. Lett. 1993, 1059-1062.
221. Yamamura, S.; Shizuri, Y.; Shigemori, H.; Okuno, Y.; Ohkubo, M. Tetrahedron 1991, 47, 635-644.
222. Shizuri, Y.; Okuno, Y.; Shigemori, H.; Yamamura, S. Tetrahedron Lett. 1987, 28, 6661-6664.
223. Shizuri, Y.; Suyama, K.; Yamamura, S. J. Chem. Soc., Chem. Commun. 1986, 63-64.
224. Shizuri, Y.; Shigemori, H.; Okuno, Y.; Yamamura, S. Chem. Lett. 1986, 2097-2100.
225. Takakura, H.; Yamamura, S. Tetrahedron Lett. 1999, 40, 299-302.
226. Takakura, H.; Yamamura, S. Tetrahedron Lett. 1998, 39, 3717-3720.
227. Maki, S.; Kosemura, S.; Yamamura, S.; Kawano, S.; Ohba, S. Chem. Lett. 1992, 651-654.
228. Maki, S.; Suzuki, T.; Kosemura, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1991, 32, 4973-4976.
229. Yoshida, K. Electrooxidation in Organic Chemistry, Krieger: Malabar, Florida 1993.
230. Dolson, M. G.; Swenton, J. S. J. Am. Chem. Soc. 1981, 103, 2361-2371.
231. Ronlán, A.; Parker, V. D. Chem. Commun. 1970, 1567-1568.
232. Gache, Y.; Simonet, J. J. Chim. Phys. 1992, 89, 1027-1035.
233. Chapuzet, J. M.; Simonet, J. Tetrahedron 1991, 47, 791-798.
234. Bechgaard, K.; Parker, V. D. J. Am. Chem. Soc. 1972, 94, 4749-4750.
235. Waldvogel, S. R.; Mirk, D. Tetrahedron Lett. 2000, 41, 4769-4772.
236. Waldvogel, S R.; Wartini, A. R.; Rasmussen, P. H.; Rebek Jr, J. Tetrahedron Lett. 1999, 40, 3515-3518.
237. Taylor, E. C.; Kienzle, F.; Robey, R. L.; McKillop, A.; Hunt, J. D. J. Am. Chem. Soc. 1971, 93, 4845-4850.
238. McKillop, A.; Hunt, J. D.; Zelesko, M. J.; Fowler, J. S.; Taylor, E. C.; McGillivray, G.; Kienzle, F. J. Am. Chem. Soc. 1971, 93, 4841-4844.
239. Elson, I. H.; Kochi, J. K. J. Am. Chem. Soc. 1973, 95, 5060-5062.
240. Bringmann, G.; Saeb, W.; Kraus, J.; Brun, R.; François, G. Tetrahedron 2000, 56, 3523-3531.
241. Finet, J.-P. Ligand Coupling Reactions With Heteroatomic Compounds, Elsevier Science Ltd., 1998; Vol. 18.
242. Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684-3691.
243. Eberson, L.; Hartshorn, M. P.; Persson, O. Acta Chem. Scand. 1995, 49, 640-644.
244. Arisawa, M.; Utsumi, S.; Nakajima, M.; Ramesh, N. G.; Tohma, H.; Kita, Y. Chem. Commun. 1999, 469-470.
245. Pelter, A.; Ward, R. S.; Venkateswarlu, R.; Kamakshi, C.; Moinuddin, S. G. A.; Subhash, P. V.; Hursthouse, M. B.; Coles, S. J.; Light, M. E. Tetrahedron 2001, 57, 7755-7763.
246. Parker, V. D.; Ronlán, A. J. Am. Chem. Soc. 1975, 97, 4714-4721.
247. Ronlán, A.; Parker, V. D. J. Org. Chem. 1974, 39, 1014-1016.
248. Ronlán, A.; Hammerich, O.; Parker, V. D. J. Am. Chem. Soc. 1973, 95, 7132-7138.
249. Hamamoto, H.; Anilkumar, G.; Tohma, H.; Kita, Y. Chem. Commun. 2002, 450-451.
250. Kita, Y.; Gyoten, M.; Ohtsubo, M.; Tohma, H.; Takada, T. Chem. Commun. 1996, 1481-1482.
251. Kerr, J. B.; Jempty, T. C.; Miller, L. L. J. Am. Chem. Soc. 1979, 101, 7338-7346.
252. Falck, J. R.; Miller, L. L.; Stermitz, F. R. J. Am. Chem. Soc. 1974, 96, 2981-2986.
253. Tanaka, M.; Mukaiyama, C.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. J. Org. Chem. 1995, 60, 4339-4352.
254. Tanaka, M.; Ikeya, Y.; Mitsuhashi, H.; Maruno, M.; Wakamatsu, T. Tetrahedron 1995, 51, 11703-11724.
255. Tomioka, K.; Kubota, Y.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1989, 30, 2949-2952.
256. Buckleton, J. S.; Cambie, R. C.; Clark, G. R.; Craw, P. A.; Richard, C. E. F.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1988, 41, 305-324.
257. Herrero, M. T.; Tellitu, I.; Domínguez, E.; Hernandez, S.; Moreno, I.; SanMartín, R. Tetrahedron 2002, 58, 8581-8589.
258. Moreno, I.; Tellitu, I.; SanMartín, R.; Domínguez, E. Synlett 2001, 1161-1163.
259. Moreno, I.; Tellitu, I.; SanMartín, R.; Badia, D.; Carrillo, L.; Domíguez, E. Tetrahedron Lett. 1999, 40, 5067-5070.
260. Olivera, R.; SanMartín, R.; Domíguez, E. J. Org. Chem. 2000, 65, 7010-7019.
261. Olivera, R.; SanMartín, R.; Pascual, S.; Herrero, M.; Domínguez, E. Tetrahedron Lett. 1999, 40, 3479-3480.
262. Moreno, I.; Tellitu, I.; Etayo, J.; SanMartín, R.; Domíminguez, E. Tetrahedron 2001, 57, 5403-5411.
263. Eilenberg, W.; Schäfer, H. J. Tetrahedron Lett. 1984, 25, 5023-5026.
264. Venkateswarlu, R.; Kamakshi, C.; Moinuddin, S. G. A.; Subhash, P. V.; Ward, R. S.; Pelter, A.; Hursthouse, M. B.; Light, M. E. Tetrahedron 1999, 55, 13087-13108.
265. Pelter, A.; Ward, R. S.; Venkateswarlu, R.; Kamakshi, C. Tetrahedron 1991, 47, 1275-1284.
266. Kotani, E.; Takeuchi, N.; Tobinaga, S. J. Chem. Soc., Perkin Trans. 1 1973, 550-551.
267. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Kikuchi, K.; Yakura, T. Tetrahedron Lett. 1991, 32, 2035-2038.
268. Kita, Y.; Yakura, T.; Tohma, H.; Kikuchi, K.; Tamura, Y. Tetrahedron Lett. 1989, 30, 1119-1120.
269. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114, 2175-2180.