Hypervalent iodine-mediated phenol dearomatization in natural product synthesis

Tetrahedron

Volumn 66, Issue 13, 2010, Pages 2235-2261

  Pouységu, Laurent ^a   Deffieux, Denis ^a   Quideau, Stéphane ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE; NATURAL PRODUCT; PHENOL DERIVATIVE;

AROMATIZATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 77349122065     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.12.046     Document Type: Review

References (263)

1. In: Rappoport Z. (Ed). The Chemistry of Phenols (Patai Series: The Chemistry of Functional Groups) (2003), Wiley, Chichester, UK Parts 1 and 2
2. Coordination to transition metals can be used to capture nonaromatic phenol tautomers, see:
3. Todd M.A., Sabat M., Myers W.H., Smith T.M., and Harman W.D. J. Am. Chem. Soc. 130 (2008) 6906-6907
4. Todd M.A., Sabat M., Myers W.H., and Harman W.D. J. Am. Chem. Soc. 129 (2007) 11010-11011
5. Amouri H., Le Bras J., and Vaissermann J. Organometallics 17 (1998) 5850-5857 For review articles on this topic, see:
6. Amouri H., and Le Bras J. Acc. Chem. Res. 35 (2002) 501-510
7. Smith P.L., Chordia M.D., and Harman W.D. Tetrahedron 57 (2001) 8203-8225
8. Harman W.D. Chem. Rev. 97 (1997) 1953-1978
9. Shiner C.S., Vorndam P.E., and Kass S.R. J. Am. Chem. Soc. 108 (1986) 5699-5701 See also:
10. Santoro D., and Louw R. J. Chem. Soc., Perkin Trans. 2 (2001) 645-649
11. Mulder P., Korth H.-G., Pratt D.A., DiLabio G.A., Valgimigli L., Pedulli G.F., and Ingold K.U. J. Phys. Chem. A 109 (2005) 2647-2655
12. Blanksby S.J., and Ellison G.B. Acc. Chem. Res. 36 (2003) 255-263
13. Ralph J., Brunow G., Harris P.J., Dixon R.A., Schatz P.F., and Boerjan W. In: Daayf F., and Lattanzio V. (Eds). Recent Advances in Polyphenol Research Vol. 1 (2008), Wiley-Blackwell, Oxford, UK 36-66 and references cited therein
14. Leopoldini M., Marino T., Ruso N., and Toscano M. J. Phys. Chem. A 108 (2004) 4916-4922
15. Wright J.S., Johnson E.R., and DiLabio G.A. J. Am. Chem. Soc. 123 (2001) 1173-1183
16. Pietta P.-G. J. Nat. Prod. 63 (2000) 1035-1042
17. Bors W., and Michel C. Free Radical Biol. Med. 27 (1999) 1413-1426
18. Magdziak D., Meek S.J., and Pettus T.R.R. Chem. Rev. 104 (2004) 1383-1429
19. Quideau S., Pouységu L., and Deffieux D. Synlett (2008) 467-495
20. Quideau S., Pouységu L., and Deffieux D. Curr. Org. Chem. 8 (2004) 113-148 and references cited therein
21. Rodriguez S., and Wipf P. Synthesis (2004) 2767-2783
22. Quideau S. In: Astruc D. (Ed). Modern Arene Chemistry (2002), Wiley-VCH, Weinheim 539-573
23. Quideau S., and Feldman K.S. Tetrahedron 57 (2001) ix-x
24. Quideau S., and Pouységu L. Org. Prep. Proced. Int. 31 (1999) 617-680
25. Waring A.J. In: Hart H., and Karabatsos G.J. (Eds). Adances in Alicyclic Chemistry Vol. 1 (1966), Academic, New York, NY, London 129-256 and references cited therein
26. Miller B. In: Thyagarajan B.S. (Ed). Mechanisms of Molecular Migrations Vol. 1 (1968), Wiley, New York, NY 247-313 and references cited therein
27. Miller B. J. Org. Chem. 35 (1970) 4262-4264
28. For recent applications of the dearomatizing phenol O-allylation/Claisen rearrangement sequence in natural product synthesis, see:
29. Nicolaou K.C., Xu H., and Wartmann M. Angew. Chem. Int. Ed. 44 (2005) 756-761
30. Pettus T.R.R., Inoue M., Chen X.-T., and Danishefsky S.J. J. Am. Chem. Soc. 122 (2000) 6160-6168
31. Zhdankin V.V., and Stang P.J. Chem. Rev. 108 (2008) 5299-5358
32. In: Wirth T. (Ed). Hypervalent Iodine Chemistry-Modern Developments in Organic Synthesis (Topics in Current Chemistry) Vol. 224 (2003), Springer, Berlin, Heidelberg
33. Moriarty R.M., and Prakash O. Org. React. 57 (2001) 327-415
34. Varvoglis A. In: Katritsky A.R., Meth-Cohn O., and Rees C.W. (Eds). Hypervalent Iodine in Organic Synthesis (Best Synthetic Methods) (1997), Academic, San Diego, London
35. Siegel A., and Antony F. Monatsh. Chem. 86 (1955) 292-300
36. Szántay C., Blaskó G., Bárczai-Beke M., Péchy P., and Dörnyei G. Tetrahedron Lett. 21 (1980) 3509-3512
37. White J.D., Caravatti G., Kline T.B., and Edstrom E. Tetrahedron 39 (1983) 2393-2397
38. White J.D., Chong W.K.M., and Thirring K. J. Org. Chem. 48 (1983) 2300-2302
39. Vanderlaan D.G., and Schwartz M.A. J. Org. Chem. 50 (1985) 743-747
40. Schwartz M.A., and Pham P.T.K. J. Org. Chem. 53 (1988) 2318-2322
41. Tamura Y., Yakura T., Haruta J.-i., and Kita Y. J. Org. Chem. 52 (1987) 3927-3930
42. Lewis N., and Wallbank P. Synthesis (1987) 1103-1106
43. Pelter A., and Elgendy S. Tetrahedron Lett. 29 (1988) 677-680
44. Pelter A., and Elgendy S.M.A. J. Chem. Soc., Perkin Trans. 1 (1993) 1891-1896
45. Ochiai M. In: Wirth T. (Ed). Hypervalent Iodine Chemistry-Modern Developments in Organic Synthesis (Topics in Current Chemistry) Vol. 224 (2003), Springer, Berlin, Heidelberg 5-68
46. Okuyama T., Takino T., Sueda T., and Ochiai M. J. Am. Chem. Soc. 117 (1995) 3360-3367
47. Kida M., Sueda T., Goto S., Okuyama T., and Ochiai M. Chem. Commun. (1996) 1933-1934
48. Ochiai M. In: Akiba K.-y. (Ed). Chemistry of Hypervalent Compounds (1999), Wiley-VCH, New York, NY 359-387 See also:
49. Stang P.J., Hanack M., and Subramanian L.R. Synthesis (1982) 85-126
50. Pelter A., and Ward R.S. Tetrahedron 57 (2001) 273-282
51. Kürti L., Herczegh P., Visy J., Simonyi M., Antus S., and Pelter A. J. Chem. Soc., Perkin Trans. 1 (1999) 379-380
52. Bérard D., Racicot L., Sabot C., and Canesi S. Synlett (2008) 1076-1080
53. Dohi T., Maruyama A., Takenaga N., Senami K., Minamitsuji Y., Fujioka H., Caemmerer S.B., and Kita Y. Angew. Chem. Int. Ed. 47 (2008) 3787-3790
54. Quideau S., Looney M.A., and Pouységu L. Org. Lett. 1 (1999) 1651-1654
55. Pouységu L., Chassaing S., Dejugnac D., Lamidey A.-M., Miqueu K., Sotiropoulos J.-M., and Quideau S. Angew Chem. Int. Ed. 47 (2008) 3552-3555
56. Quideau S., Pouységu L., and Looney M.A. J. Org. Chem. 63 (1998) 9597-9600
57. Ozanne-Beaudenon A., and Quideau S. Angew. Chem. Int. Ed. 44 (2005) 7065-7069
58. Quideau S., Pouységu L., Ozanne A., and Gagnepain J. Molecules 10 (2005) 201-216
59. Finet J.-P. In: Baldwin J.E., and Williams R.M. (Eds). Ligand Coupling Reactions With Heteroatomic Compounds (Tetrahedron Organic Chemistry Series) Vol. 18 (1998), Pergamon-Elsevier Science Ltd, Oxford, UK
60. Moriarty R.M., and Vaid R.K. Synthesis (1990) 431-447
61. Schröder G., Okinaka T., Mimura Y., Watanabe M., Matsuzaki T., Hasuoka A., Yamamoto Y., Matsukawa S., and Akiba K.-Y. Chem. Eur. J. 13 (2007) 2517-2529
62. Barton D.H.R., Donnelly D.M.X., Guiry P.J., and Finet J.-P. J. Chem. Soc., Perkin Trans. 1 (1994) 2921-2926
63. Finet J.-P. Chem. Rev. 89 (1989) 1487-1501
64. Bodajla M., Jones G.R., and Ramsden C.A. Tetrahedron Lett. 38 (1997) 2573-2576
65. Magdziak D., Rodriguez A.A., Van De Water R.W., and Pettus T.R.R. Org. Lett. 4 (2002) 285-288
66. Ozanne A., Pouységu L., Depernet D., François B., and Quideau S. Org. Lett. 5 (2003) 2903-2906
67. Lebrasseur N., Gagnepain J., Ozanne-Beaudenon A., Léger J.-M., and Quideau S. J. Org. Chem. 72 (2007) 6280-6283
68. Adler E., Andersson G., and Edman E. Acta Chem. Scand. B 29 (1975) 909-920 and other papers from the same series
69. Fatiadi A.J. Synthesis (1974) 229-272
70. Ravi B.N., Perzanowski H.P., Ross R.A., Erdman T.R., Scheuer P.J., Finer A., and Clardy J. Pure Appl. Chem. 51 (1979) 1893-1900
71. Urban S., and Capon R.J. J. Nat. Prod. 59 (1996) 900-901
72. Quideau S., Lebon M., and Lamidey A.-M. Org. Lett. 4 (2002) 3975-3978
73. Dai M., and Danishefsky S.J. Heterocycles 77 (2009) 157-161
74. Dai M., and Danishefsky S.J. Tetrahedron Lett. 49 (2008) 6610-6612
75. Simmons E.M., Hardin A.R., Guo X., and Sarpong R. Angew. Chem. Int. Ed. 47 (2008) 6650-6653
76. Liu L., Gao Y., Che C., Wu N., Wang D.Z., Li C.-C., and Yang Z. Chem. Commun. (2009) 662-664
77. Frie J.L., Jeffrey C.S., and Sorensen E.J. Org. Lett. 11 (2009) 5394-5397 See also:
78. Mendelsohn B.A., Lee S., Kim S., Teyssier F., Aulakh V.S., and Ciufolini M.A. Org. Lett. 11 (2009) 1539-1542
79. Wong Y.-S. Chem. Commun. (2002) 686-687
80. Baldwin J.E., Adlington R.M., Sham V.W.-W., Marquez R., and Bulger P.G. Tetrahedron 61 (2005) 2353-2363
81. Falomir E., Alvarez-Bercedo P., Carda M., and Marco J.A. Tetrahedron Lett. 46 (2005) 8407-8410
82. Alvarez-Bercedo P., Falomir E., Carda M., and Marco J.A. Tetrahedron 62 (2006) 9641-9649
83. Peuchmaur M., and Wong Y.-S. J. Org. Chem. 72 (2007) 5374-5379
84. Wipf P., and Jung J.-K. Chem. Rev. 99 (1999) 1469-1480
85. Wipf P., Jung J.-K., Rodriguez S., and Lazo J.S. Tetrahedron 57 (2001) 283-296
86. Wipf P., and Jung J.-K. J. Org. Chem. 63 (1998) 3530-3531
87. Wipf P., and Jung J.K. J. Org. Chem. 65 (2000) 6319-6337
88. Wipf P., and Jung J.-K. J. Org. Chem. 64 (1999) 1092-1093
89. Wipf P., and Kim Y. Tetrahedron Lett. 33 (1992) 5477-5480
90. Wipf P., Kim Y., and Goldstein D.M. J. Am. Chem. Soc. 117 (1995) 11106-11112
91. Wipf P., and Methot J.-L. Org. Lett. 2 (2000) 4213-4216
92. Wipf P., Rector S.R., and Takahashi H. J. Am. Chem. Soc. 124 (2002) 14848-14849
93. Wipf P., and Spencer S.R. J. Am. Chem. Soc. 127 (2005) 225-235
94. Ciufolini M.A., Braun N.A., Canesi S., Ousmer M., Chang J., and Chai D. Synthesis (2007) 3759-3772
95. Ciufolini M.A., Canesi S., Ousmer M., and Braun N.A. Tetrahedron 62 (2006) 5318-5337
96. Ousmer M., Braun N.A., Bavoux C., Perrin M., and Ciufolini M.A. J. Am. Chem. Soc. 123 (2001) 7534-7538
97. Kita Y., Tohma H., Kikuchi K., Inagaki M., and Yakura T. J. Org. Chem. 56 (1991) 435-438
98. Ousmer M., Braun N.A., and Ciufolini M.A. Org. Lett. 3 (2001) 765-767
99. Canesi S., Bouchu D., and Ciufolini M.A. Angew. Chem. Int. Ed. 43 (2004) 4336-4338
100. Scheffler G., Seike H., and Sorensen E.J. Angew. Chem. Int. Ed. 39 (2000) 4593-4596
101. Mizutani H., Takayama J., Soeda Y., and Honda T. Tetrahedron Lett. 43 (2002) 2411-2414
102. Kita Y., Takada T., Gyoten M., Tohma H., Zenk M.H., and Eichhorn J. J. Org. Chem. 61 (1996) 5857-5864
103. Kita Y., Arisawa M., Gyoten M., Nakajima M., Hamada R., Tohma H., and Takada T. J. Org. Chem. 63 (1998) 6625-6633
104. Arisawa M., Tohma H., and Kita Y. Yakugaku Zasshi 120 (2000) 1061-1073
105. Tohma H., Morioka H., Takizawa S., Arisawa M., and Kita Y. Tetrahedron 57 (2001) 345-352
106. Harayama Y., and Kita Y. Curr. Org. Chem. 9 (2005) 1567-1588
107. Kita Y., Egi M., Takada T., and Tohma H. Synthesis (1999) 885-897
108. Tohma H., Harayama Y., Hashizume M., Iwata M., Egi M., and Kita Y. Angew. Chem. Int. Ed. 41 (2002) 348-350
109. Tohma H., Harayama Y., Hashizume M., Iwata M., Kiyono Y., Egi M., and Kita Y. J. Am. Chem. Soc. 125 (2003) 11235-11240
110. Kita Y., Tohma H., Hatanaka K., Takada T., Fujita S., Mitoh S., Sakurai H., and Oka S. J. Am. Chem. Soc. 116 (1994) 3684-3691
111. Kita Y., Tohma H., Inagaki M., Hatanaka K., and Yakura T. Tetrahedron Lett. 32 (1991) 4321-4324
112. Honda T., and Shigehisa H. Org. Lett. 8 (2006) 657-659
113. Shigehisa H., Takayama J., and Honda T. Tetrahedron Lett. 47 (2006) 7301-7306
114. Wang X., and Porco Jr. J.A. Angew. Chem. Int. Ed. 44 (2005) 3067-3071
115. Ley S.V., Baxendale I.R., and Myers R.M. In: Triggle D.J., and Taylor J.B. (Eds). Comprehensive Medicinal Chemistry Vol. 3 (2006), Elsevier, Oxford, UK 791-836
116. Ley S.V., Baxendale I.R., and Myers R.M. In: Boldi A.M. (Ed). Combinatorial Synthesis of Natural Product-Based Libraries (2006), CRC, Boca-Raton, FL 131-163
117. Baxendale I.R., and Ley S.V. Curr. Org. Chem. 9 (2005) 1521-1534
118. Ley S.V., Baxendale I.R., Brusotti G., Caldarelli M., Massi A., and Nesi M. Il Farmaco 57 (2002) 321-330
119. Ley S.V., Schucht O., Thomas A.W., and Murray P.J. J. Chem. Soc., Perkin Trans. 1 (1999) 1251-1252
120. Baxendale I.R., Deeley J., Griffiths-Jones C.M., Ley S.V., Saaby S., and Tranmer G.K. Chem. Commun. (2006) 2566-2568
121. Ley S.V., and Baxendale I.R. Chimia 62 (2008) 162-168
122. Baxendale I.R., Ley S.V., and Piutti C. Angew. Chem. Int. Ed. 41 (2002) 2194-2197
123. Baxendale I.R., Ley S.V., Nessi M., and Piutti C. Tetrahedron 58 (2002) 6285-6304
124. Baxendale I.R., and Ley S.V. Ind. Eng. Chem. Res. 44 (2005) 8588-8592
125. Guérard K.C., Sabot C., Racicot L., and Canesi S. J. Org. Chem. 74 (2009) 2039-2045
126. Sabot C., Guérard K.C., and Canesi S. Chem. Commun. (2009) 2941-2943
127. Corey E.J., and Wu L.I. J. Am. Chem. Soc. 115 (1993) 9327-9328 See also:
128. Wipf P., Kim Y., and Jahn H. Synthesis (1995) 1549-1562
129. Taylor R.J.K., Alcaraz L., Kapfer-Eyer I., Macdonald G., Wei X., and Lewis N. Synthesis (1998) 775-790
130. Hu Y., Li C., Kulkarni B.A., Strobel G., Lobkovsky E., Torczynski R.M., and Porco Jr. J.A. Org. Lett. 3 (2001) 1649-1652
131. Li C., Lobkovsky E., and Porco Jr. J.A. J. Am. Chem. Soc. 122 (2000) 10484-10485
132. Li C., Johnson R.P., and Porco Jr. J.A. J. Am. Chem. Soc. 125 (2003) 5095-5106
133. Li C., Pace E.A., Liang M.-C., Lobkovsky E., Gilmore T.D., and Porco Jr. J.A. J. Am. Chem. Soc. 123 (2001) 11308-11309
134. Li C., Bardhan S., Pace E.A., Liang M.-C., Gilmore T.D., and Porco Jr. J.A. Org. Lett. 4 (2002) 3267-3270
135. Li C., and Porco Jr. J.A. J. Org. Chem. 70 (2005) 6053-6065
136. Li C., and Porco Jr. J.A. J. Am. Chem. Soc. 126 (2004) 1310-1311
137. Lei X., Johnson R.P., and Porco Jr. J.A. Angew. Chem. Int. Ed. 42 (2003) 3913-3917
138. Porco Jr. J.A., Su S., Lei X., Bardhan S., and Rychnovsky S.D. Angew. Chem. Int. Ed. 45 (2006) 5790-5792
139. Lei X., and Porco Jr. J.A. J. Am. Chem. Soc. 128 (2006) 14790-14791
140. Carreño M.C., Gonzalez M.P., and Houk K.N. J. Org. Chem. 62 (1997) 9128-9137
141. Carreño M.C., Gonzalez M.P., Ribagorda M., and Houk K.N. J. Org. Chem. 63 (1998) 3687-3693
142. Carreño M.C., Gonzalez M.P., Ribagorda M., Somoza A., and Urbano A. Chem. Commun. (2002) 3052-3053
143. Carreño M.C., Merino E., Ribagorda M., Somoza A., and Urbano A. Org. Lett. 7 (2005) 1419-1422
144. Carreño M.C., Merino E., Ribagorda M., Somoza A., and Urbano A. Chem. Eur. J. 13 (2007) 1064-1077
145. Carreño M.C., Ribagorda M., Somoza A., and Urbano A. Angew. Chem. Int. Ed. 41 (2002) 2755-2757
146. Carreño M.C., Somoza A., Ribagorda M., and Urbano A. Chem. Eur. J. 13 (2007) 879-890
147. Yu M., and Danishefsky S.J. J. Am. Chem. Soc. 130 (2008) 2783-2785
148. Breuning M., and Corey E.J. Org. Lett. 3 (2001) 1559-1562
149. Pettus H.L., Van De Walter R.W., and Pettus T.R.R. Org. Lett. 3 (2001) 905-908
150. Van De Water R.W., Hoarau C., and Pettus T.R.R. Tetrahedron Lett. 44 (2003) 5109-5113
151. Hoarau C., and Pettus T.R.R. Org. Lett. 8 (2006) 2843-2846
152. Moriarty R.M., Gupta S.C., Hu H., Berenschot D.R., and White K.B. J. Am. Chem. Soc. 103 (1981) 686-688
153. McQuaid K.M., and Pettus T.R.R. Synlett (2004) 2403-2405
154. Lee S., and MacMillan D.W.C. Tetrahedron 62 (2006) 11413-11424
155. Basha A., Lipton M., and Weinreb S.M. Tetrahedron Lett. (1977) 4171-4174
156. Mejorado L.H., and Pettus T.R.R. J. Am. Chem. Soc. 128 (2006) 15625-15631
157. Wang J., and Pettus T.R.R. Tetrahedron Lett. 45 (2004) 5895-5899
158. Wang J., Pettus L.H., and Pettus T.R.R. Tetrahedron Lett. 45 (2004) 1793-1796
159. Benderly A., and Stavchansky S. Tetrahedron Lett. 29 (1988) 739-740
160. Wenderski T.A., Huang S., and Pettus T.R.R. J. Org. Chem. 74 (2009) 4104-4109
161. Tiefenbacher K., and Mulzer J. Angew. Chem. Int. Ed. 47 (2008) 2548-2555
162. Nicolaou K.C., Chen J.S., Edmonds D.J., and Estrada A.A. Angew. Chem. Int. Ed. 48 (2009) 660-719
163. Nicolaou K.C., Edmonds D.J., Li A., and Tria G.S. Angew. Chem. Int. Ed. 46 (2007) 3942-3945
164. Nicolaou K.C., and Chen J.S. Pure Appl. Chem. 80 (2008) 727-742
165. Quideau S., Pouységu L., Oxoby M., and Looney M. Tetrahedron 57 (2001) 319-329
166. Lebrasseur N., Fan G.-F., Oxoby M., Looney M., and Quideau S. Tetrahedron 61 (2005) 1551-1562
167. Lebrasseur N., Fan G.-J., and Quideau S. Arkivoc 13 (2004) 5-16
168. Nicolaou K.C., Tang Y., Wang J., Stepan A.F., Li A., and Montero A. J. Am. Chem. Soc. 129 (2007) 14850-14851
169. Lallic G., and Corey E.J. Org. Lett. 9 (2007) 4921-4923
170. Nicolaou K.C., Toh Q.-Y., and Chen D.Y.-K. J. Am. Chem. Soc. 130 (2008) 11292-11293
171. Gagnepain J., Méreau R., Dejugnac D., Léger J.-M., Castet F., Deffieux D., Pouységu L., and Quideau S. Tetrahedron 63 (2007) 6493-6505 and references cited therein
172. Deffieux D., Fabre I., Courseille C., and Quideau S. J. Org. Chem. 67 (2002) 4458-4465 and references cites therein
173. Deffieux D., Fabre I., Titz A., Léger J.-M., and Quideau S. J. Org. Chem. 69 (2004) 8731-8738 and references cited therein
174. Quideau S., Looney M.A., Pouységu L., Ham S., and Birney D.M. Tetrahedron Lett. 40 (1999) 615-618
175. Liao C.-C., and Peddinti R.K. Acc. Chem. Res. 35 (2002) 856-866
176. Liao C.-C. Pure Appl. Chem. 77 (2005) 1221-1234
177. Hsu D.-S., Hsu P.-Y., and Liao C.-C. Org. Lett. 3 (2001) 263-265
178. Hsu D.-S., Hsu P.-Y., Lee Y.-C., and Liao C.-C. J. Org. Chem. 73 (2008) 2554-2563
179. Hsu D.-S., and Liao C.-C. Org. Lett. 5 (2003) 4741-4743
180. Yen C.-F., and Liao C.-C. Angew. Chem. Int. Ed. 41 (2002) 4090-4093
181. Hsu D.-S., and Liao C.-C. Org. Lett. 9 (2007) 4563-4565
182. Shiao H.-Y., Hsieh H.-P., and Liao C.-C. Org. Lett. 10 (2008) 449-452
183. Snyder S.A., and Kotes F. J. Am. Chem. Soc. 131 (2009) 1745-1752
184. Yates P., and Auksi H. J. Chem. Soc., Chem. Commun. (1976) 1016-1017
185. Bichan D.J., and Yates P. Can. J. Chem. 53 (1975) 2054-2063
186. Bichan D.J., and Yates P. J. Am. Chem. Soc. 94 (1972) 4773-4774
187. Cook S.P., and Danishefsky S.J. Org. Lett. 8 (2006) 5693-5695
188. Njardarson J.T., McDonald I.M., Spiegel D.A., Inoue M., and Wood J.L. Org. Lett. 3 (2001) 2435-2438
189. Hong S.-p., and McIntosh M.C. Org. Lett. 4 (2002) 19-21
190. Li F., Tartakoff S.S., and Castle S.L. J. Am. Chem. Soc. 131 (2009) 6674-6675
191. Reeder M.D., Srikanth G.S.C., Jones S.P., and Castle S.L. Org. Lett. 7 (2005) 1089-1092
192. Yasui Y., Suzuki K., and Matsumoto T. Synlett (2004) 619-622
193. Yasui Y., Koga Y., Suzuki K., and Matsumoto T. Synlett (2004) 615-618
194. Onoda T., Takikawa Y., Fujimoto T., Yasui Y., Suzuki K., and Matsumoto T. Synlett (2009) 1041-1046
195. Mal D., and Pahari P. Chem. Rev. 107 (2007) 1892-1918
196. Hauser F.M., Dorsch W.A., and Mal D. Org. Lett. 4 (2002) 2237-2239
197. Hauser F.M., Liao H., and Sun Y. Org. Lett. 4 (2002) 2241-2243
198. Mal D., Patra A., and Roy H. Tetrahedron Lett. 45 (2004) 7895-7898
199. Kao T.C., Chuang G.J., and Liao C.-C. Angew. Chem. Int. Ed. 47 (2008) 7325-7327
200. Wood J.L., Graeber J.K., and Njardarson J.T. Tetrahedron 59 (2003) 8855-8858
201. Runcie K.A., and Taylor R.J.K. Org. Lett. 3 (2001) 3237-3239
202. Tagaki R., Miyanaga W., Tamura Y., and Ohkata K. Chem. Commun. (2002) 2096-2097
203. Pitsinos E.N., and Cruz A. Org. Lett. 7 (2005) 2245-2248
204. Arenz C., and Giannis A. Angew. Chem. Int. Ed. 39 (2000) 1440-1442
205. Arenz C., and Giannis A. Eur. J. Org. Chem. 1 (2001) 137-140
206. Arenz C., Gartner M., Wascholowski V., and Giannis A. Bioorg. Med. Chem. 9 (2001) 2901-2904
207. Burgett A.W.G., Li Q., Wei Q., and Harran P.G. Angew. Chem. Int. Ed. 42 (2003) 4961-4966
208. Sabot C., Bérard D., and Canesi S. Org. Lett. 10 (2008) 4629-4632
209. Juhasz L., Kürti L., and Antus S. J. Nat. Prod. 63 (2000) 866-870
210. Wang E.-C., Wein Y.-S., and Kuo Y.-H. Tetrahedron Lett. 47 (2006) 9195-9197
211. Huang Y., Zhang J., and Pettus T.R.R. Org. Lett. 7 (2005) 5841-5844
212. Lindsey C.C., Wu K.L., and Pettus T.R.R. Org. Lett. 8 (2006) 2365-2367
213. Marsini M.A., Gowin K.M., and Pettus T.R.R. Org. Lett. 8 (2006) 3481-3483
214. Zhu J., Germain A.R., and Porco Jr. J.A. Angew. Chem. Int. Ed. 43 (2004) 1239-1243
215. Quideau S., Pouységu L., Deffieux D., Ozanne A., Gagnepain J., Fabre I., and Oxoby M. Arkivoc 6 (2003) 106-119
216. Soga O., Iwamoto H., Oota Y., Oiie Y., Takuwa A., Nozaki H., Kuramoto J., and Nakayama M. 27th Symposium on the Chemistry of Natural Products (1985), Hiroshima, Japan p 687
217. Pouységu L., Marguerit M., Gagnepain J., Lyvinec G., Eatherton A.J., and Quideau S. Org. Lett. 10 (2008) 5211-5214
218. Yuan Y., Men H., and Lee C. J. Am. Chem. Soc. 126 (2004) 14720-14721
219. Smith A.B., Mesaros E.F., and Meyer E.A. J. Am. Chem. Soc. 128 (2006) 5292-5299
220. Smith A.B., Mesaros E.F., and Meyer E.A. J. Am. Chem. Soc. 127 (2005) 6948-6949
221. Lowe J.T., and Panek J.S. Org. Lett. 10 (2008) 3813-3816
222. Kuboki A., Yamamoto T., and Ohira S. Chem. Lett. 32 (2003) 420-421
223. Kuboki A., Yamamoto T., Taira M., Arishige T., and Ohira S. Tetrahedron Lett. 48 (2007) 771-774
224. Kuboki A., Yamamoto T., Taira M., Arishige T., Konishi R., Hamabata M., Shirahama M., Hiramatsu T., Kuyama K., and Ohira S. Tetrahedron Lett. 49 (2008) 2558-2561
225. Kuboki A., Maeda C., Arishige T., Kuyama K., Hamabata M., and Ohira S. Tetrahedron Lett. 49 (2008) 4516-4518
226. Andersson G. Acta Chem. Scand. B 30 (1976) 64-70
227. Andersson G. Acta Chem. Scand. B 30 (1976) 403-406
228. Lai C.-H., Shen Y.-L., and Liao C.-C. Synlett (1997) 1351-1352
229. Metlesics W., and Wessely W. Monatsh. Chem. 88 (1957) 108-117
230. Quideau S., Pouységu L., Avellan A.-V., Whelligan D.K., and Looney M.A. Tetrahedron Lett. 42 (2001) 7393-7396
231. Pouységu L., Avellan A.-V., and Quideau S. J. Org. Chem. 67 (2002) 3425-3436
232. Andersson G., and Berntsson P. Acta Chem. Scand. B 29 (1975) 948-952
233. Liao C.-C., Chu C.-S., Lee T.-H., Rao P.D., Ko S., Song L.-D., and Shiao H.-C. J. Org. Chem. 64 (1999) 4102-4110
234. Su B.-N., Yang L., Gao K., and Jia Z.-J. Planta Med. 66 (2000) 281-283
235. Su B.-N., Zhu Q.-X., and Jia Z.-J. Tetrahedron Lett. 40 (1999) 357-358
236. Gagnepain J., Castet F., and Quideau S. Angew. Chem. Int. Ed. 46 (2007) 1533-1535
237. Angew. Chem. Int. Ed. 47 (2008) 628
238. Carman R.M., Lambert L.K., Robinson W.T., and Van Dongen J.M.A.M. Aust. J. Chem. 39 (1986) 1843-1850
239. Liao Y.-H., Xu L.-Z., Yang S.-H., Dai J., Zhen Y.-S., Zhu M., and Sun N.-J. Phytochemistry 45 (1997) 729-732
240. Bérubé A., Drutu I., and Wood J.L. Org. Lett. 8 (2006) 5421-5424
241. Quideau S., Fabre I., and Deffieux D. Org. Lett. 6 (2004) 4571-4573
242. Singh V. Acc. Chem. Res. 32 (1999) 324-333
243. Singh V., and Thomas B. Tetrahedron 54 (1998) 3647-3692
244. Singh V., Chandra G., and Mobin S.M. Synthesis (2008) 2719-2728
245. Singh V., Samanta B., and Kane V.V. Tetrahedron 56 (2000) 7785-7795
246. Singh V., and Samanta B. Tetrahedron Lett. 40 (1999) 383-386
247. Singh V., Vedantham P., and Sahu P.K. Tetrahedron Lett. 43 (2002) 519-522
248. Singh V., Pal S., Tosh D.K., and Mobin S.M. Tetrahedron 63 (2007) 2446-2454
249. Singh V., Chandra G., and Mobin S.M. Synlett (2008) 2267-2270
250. Uyanik M., and Ishihara K. Chem. Commun. (2009) 2086-2099
251. Ladziata U., and Zhdankin V.V. Synlett (2007) 527-537
252. Zhdankin V.V. Curr. Org. Chem. 2 (2005) 121-145
253. Moriarty R.M. J. Org. Chem. 70 (2005) 2893-2903
254. Wirth T. Angew. Chem. Int. Ed. 44 (2005) 3656-3665
255. Wirth T. Angew. Chem. Int. Ed. 40 (2001) 2812-2814
256. Koser G.F. Aldrichimica Acta 34 (2001) 89-102
257. Vo N.T., Pace R.D.M., O'Hara F., and Gaunt M.J. J. Am. Chem. Soc. 130 (2008) 404-405
258. Boppisetti J.K., and Birman V.B. Org. Lett. 11 (2009) 1221-1223
259. Dohi T., and Kita Y. Chem. Commun. (2009) 2073-2085
260. Ochiai M. Chem. Rec. 7 (2007) 12-23
261. Richardson R.D., and Wirth T. Angew. Chem. Int. Ed. 45 (2006) 4402-4404
262. Dohi T., Maruyama A., Minamitsuji Y., Takenaga N., and Kita Y. Chem. Commun. (2007) 1224-1226
263. Quideau S., Lyvinec G., Marguerit M., Bathany K., Ozanne-Beaudenon A., Buffeteau T., Cavagnat D., and Chénedé A. Angew. Chem. Int. Ed. 48 (2009) 4605-4609