The Claisen rearrangement in the syntheses of bioactive natural products

Tetrahedron

Volumn 69, Issue 34, 2013, Pages 6921-6957

  Majumdar, K C ^a   Nandi, Raj Kumar ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

Bioactivity; Claisen rearrangement; Isolation; Natural products; Synthesis

Indexed keywords

5 EPIVIBSANIN E; AVENACIOLIDE; COMMUNESIN F; CURVICOLLIDE A; CURVICOLLIDE B; CURVICOLLIDE C; CYCLOPENTENONE DERIVATIVE; DIHYDROTOCHUINYL ACETATE; DOLASTA 1(15),7,9 TRIEN 14 OL; ECKLONIALACTONE B; ELEUTHEROBIN; ETHISOLIDE; FRONDOSIN A; FRONDOSIN B; FRONDOSIN C; FRONDOSIN D; FRONDOSIN E; HYPERFORIN; ISOAMIJIOL; JOUBERTINAMINE; MESEMBRINE; MILBEMYCIN BETA3; NATURAL PRODUCT; PINNATOXIN A; PINNATOXIN G; SESQUITERPENE; TETRODOTOXIN; TOCHUINYL; UNCLASSIFIED DRUG; UNINDEXED DRUG; XENIOLIDE F;

AROMATIC CLAISEN REARRANGEMENT; AZA CLAISEN REARRANGEMENT; CLAISEN MISLOW EVANS REARRANGEMENT; CLAISEN REARRANGEMENT; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHENMOSER CLAISEN REARRANGEMENT; IRELAND CLAISEN REARRANGEMENT; JOHNSON CLAISEN REARRANGEMENT; PRIORITY JOURNAL; REACTION ANALYSIS; RETRO CLAISEN REARRANGEMENT; REVIEW; STRUCTURE ANALYSIS; THIO CLAISEN REARRANGEMENT;

EID: 84880136270     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.06.003     Document Type: Review

References (339)

1. L. Claisen Chem. Ber. 45 1912 3157 3166
2. P. Wipf B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 5 1991 Pergamon New York, NY 827 873
3. F.E. Ziegler Chem. Rev. 88 1988 1423 1452
4. R.P. Lutz Chem. Rev. 84 1984 205 247
5. U. Nubbemeyer Synthesis 2003 961 1008
6. H. Ito, and T. Taguchi Chem. Soc. Rev. 28 1999 43 50
7. M. Hiersemann, and L. Abraham Eur. J. Org. Chem. 2002 1461 1471
8. R.E. Ireland, and R.H. Mueller J. Am. Chem. Soc. 94 1972 5897 5898
9. R.E. Ireland, and A.K. Willard Tetrahedron Lett. 16 1975 3975 3978
10. A.E. Wick, D. Felix, K. Steen, and A. Eschenmoser Helv. Chim. Acta 47 1964 2425 2429
11. W.S. Johnson, L. Werthemann, W.R. Bartlett, T.J. Brocksom, T.-T. Li, D.J. Faulkner, and M.R. Petersen J. Am. Chem. Soc. 92 1970 741 743
12. M. Hiersemann, and U. Nubbemeyer The Claisen Rearrangement, Methods and Applications 2007 Wiley-VCH Weinheim, Germany 1 571
13. J. Zeh, and M. Hiersemann J.G. De Vries, G.A. Molander, P.A. Evans, Stereoselective Synthesis Science of Syntheses Vol. 3 2011 347 382
14. K.C. Majumdar, S. Alam, and B. Chattopadhyay Tetrahedron 64 2008 597 643
15. A.M.M. Castro Chem. Rev. 104 2004 2939 3002
16. S. Kotha, N.G. Krishna, S. Halder, and S. Misra Org. Biomol. Chem. 9 2011 5597 5624
17. G.E. Veitch, A. Boyer, and S.V. Ley Angew. Chem., Int. Ed. 47 2008 9402 9429
18. F.E. Ziegler Acc. Chem. Res. 10 1977 227 232
19. Y. Chai, S.-p. Hong, H.A. Lindsay, C. McFarland, and M.C. McIntosh Tetrahedron 58 2002 2905 2928
20. J. Ishihara, and S. Hatakeyama Molecules 17 2012 14249 14259
21. D.O. Tymoshenko Org. Chem. 5 2008 85 95
22. E.A. Ilardi, C.E. Stivala, and A. Zakarian Chem. Soc. Rev. 38 2009 3133 3148
23. G.R. Pettit, R.H. Ode, C.L. Herald, R.B. Von Dreele, and C. Michel J. Am. Chem. Soc. 98 1976 4677 4678
24. G. Mehta, and N. Krishnamurthy Tetrahedron Lett. 28 1987 5945 5948
25. D.E. Williams, and R.J. Andersen Can. J. Chem. 65 1987 2244 2247
26. A. Srikrishna, and T.J. Reddy Tetrahedron 54 1998 8133 8140
27. Y. Tahara J. Pharm. Soc. Jpn. 29 1909 587 625
28. Y. Tahara Biochem. Z 30 1911 255 275
29. Y. Kishi, M. Aratani, T. Fukuyama, F. Nakatsubo, T. Goto, S. Inoue, H. Tanino, S. Sugiura, and H. Kakoi J. Am. Chem. Soc. 94 1972 9217 9219
30. Y. Kishi, T. Fukuyama, M. Aratani, F. Nakatsubo, T. Goto, S. Inoue, H. Tanino, S. Sugiura, and H. Kakoi J. Am. Chem. Soc. 94 1972 9219 9221
31. N. Ohyabu, T. Nishikawa, and M. Isobe J. Am. Chem. Soc. 125 2003 8798 8805
32. C. Anta, N. González, G. Santafé, J. Rodríguez, and C. Jiménez J. Nat. Prod. 65 2002 766 768
33. D. Renneberg, H. Pfander, and C.J. Leumann J. Org. Chem. 65 2000 9069 9079
34. G. Liu, T.C. Smith, and H. Pfander Tetrahedron Lett. 36 1995 4979 4982
35. A. Pollex, and M. Hiersemann Org. Lett. 7 2005 5705 5708
36. M. Koerner, and M. Hiersemann Synlett 2006 121 123
37. Q. Wang, A. Millet, and M. Hiersemann Synlett 2007 1683 1686
38. A.D. Patil, A.J. Freyer, L. Killmer, P. Offen, B. Carte, A.J. Jurewicz, and R.K. Jhonson Tetrahedron 53 1997 5047 5060
39. Y.F. Hallock, J.H. Cardellina II, and M.R. Boyd Nat. Prod. Lett. 11 1998 153 160
40. D.J. Brat, A.C. Bellail, and E.G. Van Meir Neuro Oncol. 7 2005 122 133
41. Y.M. Zhu, S.J. Webster, D. Flower, and P.J. Woll Br. J. Cancer 91 2004 1970 1976
42. A. Yuan, J.J. Chen, P.L. Yao, and P.C. Yang Front. Biosci. 2005 853 865
43. B.R. Lane, K. Lore, P.J. Bock, J. Andersson, M.J. Coffey, R.M. Strieter, and D.M. Markovitz J. Virol. 75 2001 8195 8202
44. X. Li, and T.V. Ovaska Org. Lett. 9 2007 3837 3840
45. T.V. Ovaska Arkivoc v 2011 34 44
46. Y. Fukuyama, H. Minami, A. Matsuo, K. Kitamura, M. Akizuki, M. Kubo, and M. Kodama Chem. Pharm. Bull. 50 2002 368 371
47. B.D. Schwartz, J.R. Denton, Y. Lian, H.M.L. Davies, and C.M. Williams J. Am. Chem. Soc. 131 2009 8329 8332
48. A.I. Gurevich, V.N. Dobrynin, M.N. Kolosov, S.A. Popravko, I.D. Ryabova, B.K. Chernov, N.A. Derbentseva, B.E. Aizenman, and A.D. Garagulya Antibiotiki 16 1971 510 513
49. C. Gey, S. Kyrylenko, L. Henning, L.D. Nguyen, A. Büttner, H.D. Pham, and A. Giannis Angew. Chem. 119 2007 5311 5314
50. Angew. Chem., Int. Ed. 46 2007 5219 5222
51. L. Verotta, G. Appendino, E. Bombardelli, and R. Brun Bioorg. Med. Chem. Lett. 17 2007 1544 1548
52. L.B. Moore, B. Goodwin, S.A. Jones, G.B. Wisely, C.J. Serabjit-Singh, T.M. Willson, J.L. Collins, and S.A. Kliewer Proc. Natl. Acad. Sci. U.S.A. 97 2000 7500 7502
53. Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 49 2010 1103 1106
54. S.J. Spessard, and B.M. Stoltz Org. Lett. 4 2002 1943 1946
55. T. Lindel, P.R. Jensen, W. Fenical, B.H. Long, A.M. Casazza, J. Carboni, and C.R. Fairchild J. Am. Chem. Soc. 119 1997 8744 8745
56. W. H. Fenical, P. R. Jensen, T. Lindel, U.S. Patent 5,473,057, 1995
57. [ Chem. Abstr. 124 1996 194297 ]
58. S.Y.F. Mak, G.C.H. Chiang, J.E.P. Davidson, J.E. Davies, A. Ayscough, G. Pain, J.W. Burton, and A.B. Holmes Tetrahedron: Asymmetry 20 2009 921 924
59. L.S.-M. Wong, K.A. Turner, J.M. White, A.B. Holmes, and J.H. Ryan Aust. J. Chem. 63 2010 529 532
60. S.Y.F. Mak, N.R. Curtis, A.N. Payne, M.S. Congreve, A.J. Wildsmith, C.L. Francis, J.E. Davies, S.I. Pascu, J.W. Burton, and A.B. Holmes Chem. - Eur. J. 14 2008 2867 2885
61. S.Y.F. Mak, N.R. Curtis, A.N. Payne, M.S. Congreve, C.L. Francis, J.W. Burton, and A.B. Holmes Synthesis 19 2005 3199 3201
62. S. Zheng, F. Huang, S. Chen, X. Tan, J. Zuo, J. Peng, and R. Xie Chin. J. Mar. Drugs 9 1990 33 35
63. For a review on bis-spiroketal systems, see: M.A. Brimble, and D.P. Furkert Curr. Org. Chem. 7 2003 1461 1484
64. S. Beaumont, E.A. Ilardi, N.D.C. Tappin, and A. Zakarian Eur. J. Org. Chem. 2010 5743 5765
65. D. Uemura, T. Chuo, T. Haino, A. Nagatsu, S. Fukuzawa, S. Zheng, and H. Chen J. Am. Chem. Soc. 117 1995 1155 1156
66. K.F. Smith, L.L. Rhodes, S. Suda, and A.I. Selwood Harmful Algae 10 2011 702 711
67. M.J. Pelc, and A. Zakarian Org. Lett. 7 2005 1629 1631
68. C.E. Stivala, and A. Zakarian J. Am. Chem. Soc. 130 2008 3774 3776
69. M.J. Pelc, and A. Zakarian Tetrahedron Lett. 47 2006 7519 7523
70. M.T. Smith, N. Crouch, N. Gericke, and M. Hirst J. Ethnopharmacol. 50 1996 119 130
71. N. P. Gericke, B. -E. Van Wyk, PCT Int. Appl., WO 9746234 CAN 128: 80030, 1997.
72. E.A. Ilardi, M.J. Isaacman, Y.-C. Qin, S.A. Shelly, and A. Zakarian Tetrahedron 65 2009 3261 3269
73. I. Kerzaon, Y.F. Pouchus, F. Monteau, B. Le Bizec, and M.R. Nourrisson Rapid Commun. Mass Spectrom. 23 2009 3928 3938
74. J. Yang, H. Wu, L. Shen, and Y. Qin J. Am. Chem. Soc. 129 2007 13794 13795
75. D.R. Williams, B.A. Barner, K. Nishitani, and J.G. Phillips J. Am. Chem. Soc. 104 1982 4708 4710
76. W.L. Shoop, H. Mrozik, and M.H. Fisher Vet. Parasitol. 59 1995 139 156
77. A. Aoki J. Pestic. Sci. 19 1992 245 247
78. S. Chamberland, M. Lee, O. Lomovskaya, Milbemycin Class Efflux Pump Inhibitors for Treating Microbial Infections and Cancer. WO 98-US20916 19981001, 1999; AN1999:244572.
79. M. Li, and G.A. O'Doherty Org. Lett. 8 2006 3987 3990
80. S.G. Nelson, C.J. Bungard, and K. Wang J. Am. Chem. Soc. 125 2003 13000 13001
81. S.G. Nelson, and K. Wang J. Am. Chem. Soc. 128 2006 4232 4233
82. H.-F. Tseou, and Y.-T. Wang J. Chin. Chem. Soc. 5 1937 224 229
83. Isolation and structure of ethisolide and isoavenaciolide
84. D.C. Aldridge, and W.B. Turner J. Chem. Soc. C 1971 2431 2432
85. D. Brookes, B.K. Tidd, and W.B. Turner J. Chem. Soc. 1963 5385 5391
86. J.J. Ellis, F.H. Stodola, R.F. Vesonder, and C.A. Glass Nature (London) 203 1964 1382 1383
87. D. Brookes, S. Stemhell, B.K. Tidd, and W.B. Turner Aust. J. Chem. 18 1965 373 377
88. D.L. Hughes Acta Crystallogr. B34 1978 3674 3678
89. J. Meyer, and P.M. Vignais Biochim. Biophys. Acta 325 1973 375 384
90. J.D. McGivan, and J.B. Chappell Biochem. J. 116 1970 37 38
91. S.D. Burke, G.J. Pacofsky, and A.D. Piscopio J. Org. Chem. 57 1992 2228 2235
92. D.L. Klyman, A. Lin, N. Acton, J.P. Scovill, J.M. Hoch, W.K. Milhous, and A.D. Theoharides J. Nat. Prod. 47 1984 715 717
93. M.A. Avery, W.K.M. Chong, and C. Jennings-White J. Am. Chem. Soc. 114 1992 974 979
94. S. Umezawa, T. Usui, H. Umezawa, T. Tsuchiya, T. Takeuchi, and M. Hamada J. Antibiot. 24 1971 85 92
95. H. Itazaki, K. Nagashima, Y. Kawamura, K. Matsumoto, H. Nakai, and Y. Terui J. Antibiot. 45 1992 38 49
96. K. Tanaka, H. Itazaki, and T. Yoshida J. Antibiot. 45 1992 50 55
97. R.D. Florio, and M.A. Rizzacasa J. Org. Chem. 63 1998 8595 8598
98. G.R. Pettit, V. Gaddamidi, G.M. Cragg, D.L. Herald, and Y. Sagawa J. Chem. Soc., Chem. Commun. 1984 1693 1694
99. G.R. Pettit, V. Gaddamidi, and G.M. Cragg J. Nat. Prod. 47 1984 1018 1020
100. S. Danishefsky, and J.Y. Lee J. Am. Chem. Soc. 111 1989 4829 4837
101. X. Tian, T. Hudlicky, and K. Königsberger J. Am. Chem. Soc. 117 1995 3643 3644
102. B.M. Trost, and S.R. Pulley J. Am. Chem. Soc. 117 1995 10143 10144
103. T.J. Doyle, M. Hendrix, D. VanDerveer, S. Javanmard, and J. Haseltine Tetrahedron 53 1997 11153 11170
104. P. Magnus, and I.K. Sebhat J. Am. Chem. Soc. 120 1998 5341 5342
105. P. Magnus, and I.K. Sebhat Tetrahedron 54 1998 15509 15524
106. J.H. Rigby, and M.E. Mateo J. Am. Chem. Soc. 119 1997 12655 12656
107. J.H. Rigby, U.S.M. Maharoof, and M.E. Mateo J. Am. Chem. Soc. 122 2000 6624 6628
108. G.R. Pettit, N. Melody, and D. Herald J. Org. Chem. 66 2001 2583 2587
109. H. Ko, E. Kim, J.E. Park, D. Kim, and S. Kim J. Org. Chem 69 2004 112 121
110. S. Hwang, D. Kim, and S. Kim Chem. - Eur. J. 18 2012 9977 9982
111. K. Müller Appl. Microbiol. Biotechnol. 56 2001 9 16
112. B.K. Park, M. Nakagawa, A. Hirota, and M. Nakayama J. Antibiot. 41 1988 751 758
113. N. Petragnani, H.M.C. Ferraz, and G.V.J. Silva Synthesis 1986 157 183
114. H.M.R. Hoffmann, and J. Rabe Angew. Chem., Int. Ed. Engl. 24 1985 94 110
115. S.B. Mahato, K.A.I. Siddiqui, G. Bhattacharya, T. Ghosal, K. Miyahara, M. Sholichin, and T. Kawasaki J. Nat. Prod. 50 1987 245 247
116. S. Drioli, F. Felluga, C. Forzato, P. Nitti, G. Pitacco, and E. Valentin J. Org. Chem. 63 1998 2385 2388
117. M. Amador, X. Ariza, J. Garcia, and J. Ortiz J. Org. Chem. 69 2004 8172 8175
118. A. Srikrishna, and B.V. Lakshmi Tetrahedron Lett. 46 2005 7029 7031
119. P. Kleinwachter, B. Schlegel, H. Dorfelt, and U. Grafe J. Antibiot. 54 2001 526 527
120. J.D. Bu'Lock, and J. Darbyshire Phytochemistry 15 1976 2004
121. C.B. Bottom, and D.J. Siehr Phytochemistry 14 1975 1433 1436
122. H. Achenbach, and B. Raffelsberger Z. Naturforsch., B 35 1980 219 225
123. S. Höck, F. Koch, and H.-J. Borschberg Tetrahedron: Asymmetry 15 2004 1801 1808
124. S. Höck, and H.-J. Borschberg Helv. Chim. Acta 89 2006 542 557
125. B. Tashkhodzhaev, K. Samikov, M.R. Yagudaev, T.P. Antsupova, R. Shakirov, and S.Y. Yunusov Khimiya 5 1985 687 691
126. K. Samikov, R. Shakirov, T.P. Antsupova, and S.Y. Yunusov Khim. Prir. Soedin. 3 1986 383
127. T. Kawasaki, W. Takamiya, N. Okamoto, M. Nagaoka, and T. Hirayama Tetrahedron Lett. 47 2006 5379 5382
128. J. Finer, J. Clardy, W. Fenical, L. Minale, R. Riccio, J. Battaile, M. Kirkup, and R.E. Moore J. Org. Chem. 44 1979 2044 2048
129. D.R. Williams, M.J. Walsh, and N.A. Miller J. Am. Chem. Soc. 131 2009 9038 9045
130. T. Diyabalanage, C.D. Amsler, J.B. McClintock, and B.J. Baker J. Am. Chem. Soc. 128 2006 5630 5631
131. M.D. Lebar, and B.J. Baker Tetrahedron Lett. 48 2007 8009 8010
132. Baker, B.; Diyabalanage, T.; Mcclintock, J. B.; Amsler, Charles D. U.S. Patent Appl. Publ., US 20,090,192,215 A1 20090730, 2009.
133. M. Penner, V. Rauniyar, L.T. Kaspar, and D.G. Hall J. Am. Chem. Soc. 131 2009 14216 14217
134. I.L. de Albuquerque, C. Galeffi, C.G. Casinovi, and G.B. Marini-Bettolo Gazz. Chim. Ital. 94 1964 287 295
135. C. Galeffi, C. Giulio Casinovi, and G.B. Marini-Bettolo Gazz. Chim. Ital. 95 1965 95 100
136. A.A. Craveiro, A.d.C. Prado, O.R. Gottlieb, and P.C. Welerson de Albuquerque Phytochemistry 9 1970 1869 1875
137. C.A.C. Araujo, L.V. Alefrio, and L.L. Leon Phytochemistry 49 1998 751 754
138. F. Colobert, R.D. Mazery, G. Solladie, and M.C. Carreno Org. Lett. 4 2002 1723 1725
139. M.C. Carreno, R.D. Mazery, A. Urbano, F. Colobert, and G. Solladie J. Org. Chem. 68 2003 7779 7787
140. W. Chazadaj, R. Kowalczyk, and J. Jurczak J. Org. Chem. 75 2010 1740 1743
141. J.J. Rubal, F.J. Moreno-Dorado, F.M. Guerra, Z.D. Jorge, A. Saouf, M. Akssira, F. Mellouki, R. Romero-Garrido, and G.M. Massanet Phytochemistry 68 2007 2480 2486
142. A. Saouf, F.M. Guerra, J.J. Rubal, F.J. Moreno-Dorado, M. Akssira, F. Mellouki, M. Lopez, A.J. Pujadas, Z.D. Jorge, and G.M. Massanet Org. Lett. 7 2005 881 884
143. G. Appendino, S. Prosperini, C. Valdivia, M. Ballero, G. Colombano, R.A. Billington, A.A. Genazzani, and O. Sterner J. Nat. Prod. 68 2005 1213 1217
144. C. Navarrete, R. Sancho, F.J. Caballero, F. Pollastro, B.L. Fiebich, O. Sterner, G. Appendino, and E. Munoz J. Pharmacol. Exp. Ther. 319 2006 422 430
145. H.M. Nelson, and B.M. Stoltz Org. Lett. 10 2008 25 28
146. M.V. Kozytska, and G.B. Dudley Tetrahedron Lett. 49 2008 2899 2901
147. Z. Xiongfei, W. Wanqing, L. Xiaozu, and L. Chi-Sing Org. Lett. 10 2008 5525 5528
148. H.M. Nelson, and B.M. Stoltz Tetrahedron Lett. 50 2009 1699 1701
149. R. Larsson, O. Sterner, and M. Johansson Org. Lett. 11 2009 657 660
150. H.M. Nelson, K. Murakami, S.C. Virgil, and B.M. Stoltz Angew. Chem., Int. Ed. 50 2011 3688 3691
151. J.Y. Cho, P.G. Williams, H.C. Kwon, P.R. Jensen, and W. Fenical J. Nat. Prod. 70 2007 1321 1328
152. U. Pal, S. Ranatunga, Y. Ariyarathna, and J.R. Del Valle Org. Lett. 11 2009 5298 5301
153. S. Ranatunga, J.S. Kim, U. Pal, and J.R. Del Valle J. Org. Chem. 76 2011 8962 8976
154. R. Araoz, D. Servent, J. Molgó, B.I. Iorga, C. Fruchart-Gaillard, E. Benoit, Z. Gu, C. Stivala, and A. Zakarian J. Am. Chem. Soc. 133 2011 10499 10511
155. Y.-C. Qin, C.E. Stivala, and A. Zakarian Angew. Chem., Int. Ed. 46 2007 7466 7469
156. T. Fujita, N. Hamamichi, M. Kiuchi, T. Matsuzaki, Y. Kitao, K. Inoue, R. Hirose, M. Yoneta, S. Sasaki, and K. Chiba J. Antibiot. 49 1996 846 853
157. N.W.G. Fairhurst, M.F. Mahon, R.H. Munday, and D.R. Carbery Org. Lett. 14 2012 756 759
158. J. Mann Nat. Prod. Rep. 18 2001 417 430
159. A.A. Stierle, D.B. Stierle, and K. Kelly J. Org. Chem. 71 2006 5357 5360
160. A.A. Stierle, and D.B. Stierle Atta-ur-Rahman Bioactive Natural Products (Part L) Studies in Natural Product Chemistry Vol. 32 2005 1123 1175
161. P.F. Godenschwager, and D.B. Collum J. Am. Chem. Soc. 130 2008 8726 8735
162. P.F. Godenschwager, and D.B. Collum J. Am. Chem. Soc. 129 2007 12023 12031
163. T.N. Snaddon, P. Buchgraber, S. Schulthoff, C. Wirtz, R. Richard Mynott, and A. Fürstner Chem. - Eur. J. 16 2010 12133 12140
164. P. Buchgraber, T.N. Snaddon, C. Wirtz, R. Mynott, R. Goddard, and A. Fürstner Angew. Chem., Int. Ed. 47 2008 8450 8454
165. N. Kawahara, M. Nozawa, A. Kurata, T. Hakamatsuka, S. Sekita, and M. Satake Chem. Pharm. Bull. 47 1999 1344 1345
166. M.S. Wilson, J.C.S. Woo, and G.R. Dake J. Org. Chem. 71 2006 4237 4245
167. R. Santi, and S. Luciani Atractyloside: Chemistry, Biochemistry and Toxicology 1978 Piccin Medical Books Padova, Italy
168. E.J. Corey, A. Guzman-Perez, and S.E. Lazerwith J. Am. Chem. Soc. 119 1997 11769 11776
169. J.M. Hutchison, A.S. Gibson, D.T. Williams, and M.C. McIntosh Tetrahedron Lett. 52 2011 6349 6351
170. Isolation: T. Fehr, J.J. Sanglier, W. Schuler, L. Gschwind, M. Ponelle, W. Schilling, and C. Wioland J. Antibiot. 49 1996 230 233
171. G.R. Pettit, J.-P. Xu, F. Hogan, M.D. Williams, D.L. Doubek, J.M. Schmidt, R.L. Cerny, and M.R. Boyd J. Nat. Prod. 60 1997 752 754
172. G.R. Pettit, T.H. Smith, J.-P. Xu, D.L. Herald, E.J. Flahive, C.R. Anderson, P.E. Belcher, and J.C. Knight J. Nat. Prod. 74 2011 1003 1008
173. K. Umezawa Adv. Enzyme Regul. 35 1995 43 53
174. Y. Baba, M. Tsukuda, I. Mochimatsu, S. Furukawa, H. Kagata, Y. Nagashima, N. Sakai, S. Koshika, M. Imoto, and Y. Kato Clin. Exp. Metastasis 18 2000 273 279
175. M. Imoto, K. Umezawa, Y. Takahashi, H. Naganawa, Y. Iitaka, H. Nakamura, Y. Koizumi, Y. Sasaki, M. Hamada, T. Sawa, and T. Takeuchi J. Nat. Prod. 53 1990 825 829
176. H. Odai, K. Shindo, A. Odagawa, J. Mochizuki, M. Hamada, and T. Takeuchi J. Antibiot. 47 1994 939 941
177. N.O. Fuller, and J.P. Morken Org. Lett. 7 2005 4867 4869
178. A.S. Rao, A. Paul, D. Sadgopal, and S.C. Bhattacharyya Tetrahedron 13 1961 319 323
179. S. Stanley Raucher, K.-W. Chi, K.-J. Hwang, and J. Burks Eur. J. Org. Chem. 51 1986 5503 5505
180. V. Hellwig, J. Dasenbrock, S. Schumann, W. Steglich, K. Leonhardt, and T. Anke Eur. J. Org. Chem. 1998 73 79
181. A. Srikrishna, and D.H. Dethe Org. Lett. 5 2003 2295 2298
182. A. Srikrishna, and N.C. Babu Tetrahedron Lett. 42 2001 4913 4914
183. T. Kajimoto, M. Yamashita, Y. Imamura, T. Nohara, and M. Shibata Chem. Lett. 1989 527 530
184. R.H. Thomson Naturally Occurring Quinones 1971 Academic Press New York pp 248-251
185. H. Nishikawa Agric. Biol. Chem. 26 1962 696
186. S. Takai Phytopathol. Zeit. 43 1962 175 182
187. A. Srikrishna, and P.C. Ravikumar Tetrahedron 62 2006 9393 9402
188. L. Nyembo, A. Goffin, C. Hootelé, and J.-C. Braekman Can. J. Chem. 56 1978 851 856
189. H. Morita, Y. Hirasawa, T. Shinzato, and J. Kobayashi Tetrahedron 60 2004 7015 7023
190. C.Y. Choo, Y. Hirasawa, C. Karimata, K. Koyama, M. Sekiguchi, J. Kobayashi, and H. Morita Bioorg. Med. Chem. 15 2007 1703 1707
191. K. Katakawa, M. Kitajima, K. Yamaguchi, and H. Takayama Heterocycles 69 2006 223 229
192. T. Shigeyama, K. Katakawa, N. Kogure, M. Kitajima, and H. Takayama Org. Lett. 9 2007 4069 4072
193. T. Tanaka, N. Kogure, M. Kitajima, and H. Takayama J. Org. Chem. 74 2009 8675 8680
194. Y. Hori, Y. Abe, N. Shigematsu, T. Goto, M. Okuhara, and M. Kohsaka J. Antibiot. 46 1993 1890 1893
195. K. Shiomi, H. Iinuma, M. Hamada, H. Naganawa, M. Manabe, C. Matsuki, T. Takeuchi, and H. Umezawa J. Antibiot. 39 1986 487 493
196. K. Shiomi, H. Nakamura, H. Iinuma, H. Naganawa, T. Takeuchi, H. Umezawa, and Y. Iitaka J. Antibiot. 40 1987 1213 1219
197. K. Shiomi, H. Iinuma, H. Naganawa, K. Isshiki, T. Takeuchi, H. Umezawa, and Y. Iitaka J. Antibiot. 39 1986 494 501
198. S.A. Snyder, Z.-Y. Tang, and R. Gupta J. Am. Chem. Soc. 131 2009 5744 5745
199. P. Selig, E. Herdtweck, and T. Bach Chem. - Eur. J. 15 2009 3509 3525
200. G.A. Cordell Introduction to Alkaloids 1981 Wiley Interscience New York, NY
201. M. Hesse Alkaloide 2000 Helvetica Chimica Acta Zürich
202. H.R. Park, K. Furihata, Y. Hayakawa, and K. Shin-ya Tetrahedron Lett. 43 2002 6941 6945
203. R. Katsuta, K. Arai, A. Yajima, and T. Nukada Synlett 2012 397 400
204. F. Meerwein, G. Stopp, W. Florian, and N. Schon Liebigs Ann. Chem. 641 1961 1 39
205. K. Iguchi, K. Mori, M. Suzuki, H. Takahashi, and Y. Yamada Chem. Lett. 1986 1789 1792
206. K.H. Brieskorn, and P. Noble Phytochemistry 22 1983 187 189
207. E.P. Kündig, R. Cannas, M. Laxmisha, L. Ronggang, and S. Tchertchian J. Am. Chem. Soc. 125 2003 5642 5643
208. K.C. Majumdar Synlett 2008 2400 2411
209. D.S. Tarbell Org. React. 2 1944 1 49
210. S.J. Rhoads, and N.R. Raulins Org. React. 22 1975 1 252
211. J.J. Gajewski P.A. Grieco, Organic Synthesis in Water 1998 Blackie London, UK 82 101
212. B. Ganem Angew. Chem., Int. Ed. 35 1996 936 945
213. K. Hiratani, and M. Albrecht Chem. Soc. Rev. 37 2008 2413 2421
214. F. Muyard, A. Nouga Bissoue, F. Bévalot, F. Tillequin, P. Caballion, and J. Vaquette Phytochemistry 42 1996 1175 1179
215. Li, X.; Lee, Y. R. Abstracts of Papers, 234th ACS National Meeting, Boston, MA, United States, Aug 19-23, 2007; ORGN-835
216. R. Pernin, F. Muyard, F. Bévalot, F. Tillequin, and J. Vaquette J. Nat. Prod. 63 2000 245 247
217. N.R. Guz, P. Lorenz, and F.R. Stermitz Tetrahedron Lett. 42 2001 6491 6494
218. E. Li, R. Tian, S. Liu, X. Chen, L. Guo, and Y. Che J. Nat. Prod. 71 2008 664 668
219. C.L. Lucas, B. Lygo, A.J. Blake, W. Lewis, and C.J. Moody Chem. - Eur. J. 17 2011 1972 1978
220. G.C. Brophy, J. Mohandas, M. Slaytor, S. Sternhell, T.R. Watson, and L.A. Wilson Tetrahedron Lett. 1969 5159 5162
221. O.L. Chapman, M.R. Engel, J.P. Springer, and J.C. Clardy J. Am. Chem. Soc. 93 1971 6696 6698
222. I.R. Baxendale, A.-L. Lee, and S.V. Ley J. Chem. Soc., Perkin Trans. 1 2002 1850 1857
223. I.R. Baxendale, A.-L. Lee, and S.V. Ley Synlett 2001 1482 1484
224. I.R. Baxendale, A.-L. Lee, and S.V. Ley J. Chem. Soc., Perkin Trans. 1 2002 1850 1857
225. Y. Aramaki, K. Chiba, and M. Tada Phytochemistry 38 1995 1419 1421
226. K.C. Nicolaoua, S. Sanchini, D. Sarlah, G. Lu, T.R. Wu, D.K. Nomura, B.F. Cravatt, B. Cubitte, J.C.D.L. Torre, A.J. Hessell, and D.R. Burton Proc. Natl. Acad. Sci. U.S.A. 108 2011 6715 6720
227. D.M. Hodgson, and S. Man Chem. - Eur. J 22 2011 9731 9737
228. G.A. Kraus, and J. Wei J. Nat. Prod. 67 2004 1039 1040
229. E. Szliszka, G. Zydowicz, B. Janoszka, C. Dobosz, G. Kowalczyk-Ziomek, and W. Krol Int. J. Oncol. 38 2011 941 953
230. M.C. Marcucci, and V. Bankova Curr. Top. Phytochem. 2 1999 115 123
231. M.C. Marcucci, F. Ferreres, A. Ramalho, M. Ferreira, V. Bankova, C. Garcia, and W. Bretz Z. Naturforsch., C 55 2000 76 81
232. L. Pisco, M. Kordian, K. Peseke, H. Feist, D. Michalik, E. Estrada, J. Carvalho, G. Hamilton, D. Rando, and J. Quincoces Eur. J. Med. Chem. 41 2006 401 407
233. J.A. McIntosh, M.S. Donia, S.K. Nair, and E.W. Schmidt J. Am. Chem. Soc. 133 2011 13698 13705
234. B.M. Trost, Y. Hu, and D.B. Horne J. Am. Chem. Soc. 129 2007 11781 11790
235. S. Vogel, S. Ohmayer, G. Brunner, and J. Heilmann Bioorg. Med. Chem. 16 2008 4286 4293
236. S. Vogel, and J. Heilmann J. Nat. Prod. 71 2008 1237 1241
237. J.F. Stevens, C.L. Miranda, B. Frei, and D.R. Buhler Chem. Res. Toxicol. 16 2003 1277 1286
238. Q. Wang, Z.-H. Ding, J.-K. Liu, and Y.-T. Zheng Antiviral Res. 64 2004 189 194
239. R.S. Khupse, and P.W. Erhardt J. Nat. Prod. 70 2007 1507 1509
240. E.M. Murphy, L. Nahar, M. Byres, M. Shoeb, M. Siakalima, M.M. Rahman, A.I. Gray, and S.D. Sarker Biochem. Syst. Ecol. 32 2004 203 207
241. Y. Wei, T.Y. Zhang, and Y. Ito J. Chromatogr., A 1033 2004 373 377
242. J. Reisch, R.A. Hussain, K. Szendrei, and S.K. Adesina Pharmazie 40 1985 812 814
243. T.B. Ng, F. Liu, and Z.T. Wang Life Sci. 66 2000 709 723
244. W. He, B.-L. Zhang, S.-Y. Zhou, X.-L. Sun, and S.-Y. Zhang Synth. Commun. 37 2007 361 368
245. L.O.A. Manguro, J.O. Midiwo, W. Kraus, and I. Ugi Phytochemistry 64 2003 855 862
246. L. Guillonneau, D. Taddei, and C.J. Moody Org. Lett. 10 2008 4505 4508
247. M. Bruder, S.J. Smith, A.J. Blake, and C.J. Moody Org. Biomol. Chem. 7 2009 2127 2134
248. A. Rudi, Y. Benayahu, and Y. Kashman Org. Lett. 6 2004 4013 4016
249. Y. Venkateswarlu, D.J. Faulkner, J.L.R. Steiner, E. Corcoran, and J. Clardy J. Org. Chem. 56 1991 6271 6274
250. M. Bruder, and C.J. Moody Synlett 2008 575 577
251. P. Junior Phytochemistry 18 1979 2053 2054
252. M. Galvez-Llompart, R. Zanni, and R. Garcia-Domenech Int. J. Mol. Sci. 12 2011 9481 9503
253. M. Muscarella, M.C. Kimber, and C.J. Moody Synlett 2008 2101 2102
254. M. Bruder, P.L. Haseler, M. Muscarella, W. Lewis, and C.J. Moody J. Org. Chem. 75 2010 353 358
255. T.P. Lebold, and M.A. Kerr Synfacts 2008 903
256. M.R. Naffziger, B.O. Ashburn, J.R. Perkins, and R.G. Carter J. Org. Chem. 72 2007 9857 9865
257. T.P. Lebold, and M.A. Kerr Org. Lett. 10 2008 997 1000
258. H.-J. Knölker, and F. Wolfgang Synlett 1997 1108 1110
259. H.-J. Knölker, W. Fröhner, and A. Wagner Tetrahedron Lett. 39 1998 2947 2950
260. H.-J. Knölker, and K.R. Reddy Synlett 1999 596 598
261. R. Czerwonka, K.R. Reddy, E. Baum, and H.-J. Knölker Chem. Commun. 2006 711 713
262. C. Ito, S. Katsuno, N. Ruangrungsi, and H. Furukawa Chem. Pharm. Bull. 46 1998 344 346
263. C. Ito, S. Katsuno, M. Itoigawa, N. Ruangrungsi, T. Mukainaka, M. Okuda, Y. Kitagawa, H. Tokuda, H. Nishino, and H. Furukawa J. Nat. Prod. 63 2000 125 128
264. A.K. Jana, and D. Mal Chem. Commun. 2010 4411 4413
265. Y.-J. Kwon, M.-J. Sohn, C.-J. Zheng, and W.-G. Kim Org. Lett. 9 2007 2449 2451
266. D.R.P. Guay Ther. Clin. Risk Manage. 3 2007 513 525
267. S. Petit, Y. Duroc, V. Larue, C. Giglione, C. Leon, C. Soulama, A. Denis, F. Dardel, T. Meinnel, and I. Artaud ChemMedChem 4 2009 261 275
268. V. Larue, B. Seijo, C. Tisne, and F. Dardel Biomol. NMR Assignments 3 2009 153 155
269. P.J. Gross, and S. Bräse Chem. - Eur. J. 16 2010 12660 12667
270. M. Fujita, H. Itokawa, and Y. Sashida Chem. Pharm. Bull. 20 1972 212 213
271. Q. Song, and N.H. Fischer J. Mex. Chem. Soc. 6 1999 211 218
272. X. Cheng, N.L. Harzdorf, T. Shaw, and D. Siegel Org. Lett. 12 2010 1304 1307
273. Y. Fukuyama, Y. Otoshi, K. Miyoshi, K. Nakamura, M. Kodama, M. Nagasawa, T. Hasegawa, H. Okazaki, and M. Sugawara Tetrahedron 48 1992 377 392
274. Z.L. Kong, S.C. Tzeng, and Y.C. Liu Bioorg. Med. Chem. Lett. 15 2005 163 166 and references cited therein
275. Y. Fukuyama, K. Nakade, Y. Minoshima, R. Yokoyama, H. Zhai, and Y. Mitsumoto Bioorg. Med. Chem. Lett. 12 2002 1163 1166
276. H. Zhai, K. Nakade, Y. Mitsumoto, and Y. Fukuyama Eur. J. Pharmacol. 474 2003 199 204
277. T. Esmui, G. Makado, H. Zhai, Y. Shimizu, Y. Mitsumoto, and Y. Fukuyama Bioorg. Med. Chem. Lett. 14 2004 2621 2625
278. T. Takeya, T. Okubo, and S. Tobinaga Chem. Pharm. Bull. 34 1986 2066 2070
279. C.-M. Chen, and Y.-C. Liu Tetrahedron Lett. 50 2009 1151 1152
280. R.M. Denton, J.T. Scragg, M.A. Galofré, X. Gui, and W. Lewis Tetrahedron 66 2010 8029 8035
281. K.M. Aumann, N.L. Hungerford, and M.J. Coster Tetrahedron Lett. 52 2011 6988 6990
282. H.-Y. Huang, T. Ishikawa, C.-F. Peng, I.-L. Tsai, and I.-S. Chen J. Nat. Prod. 71 2008 1146 1151
283. B. Harrison, and P. Crews J. Org. Chem. 62 1997 2646 2648
284. M.J. Martín, F. Berrué, P. Amade, R. Fernandéz, A. Francesch, F. Reyes, and C. Cuevas J. Nat. Prod. 68 2005 1554 1555
285. F. Quartieri, L.E. Mesiano, D. Borghi, V. Desperati, C. Gennari, and G. Papeo Eur. J. Org. Chem. 2011 6794 6801
286. K. Soga, M. Kanematsu, M. Yoshida, and K. Shishido Synlett 2011 1171 1173
287. J.C. Green, S. Jimenez-Alonso, E.R. Brown, and T.R.R. Pettus Org. Lett. 13 2011 5500 5503
288. N. Lindquist, W. Fenical, G.D.V. Duyne, and J. Clardy J. Am. Chem. Soc. 113 1991 2303 2304
289. Z. Cruz-Monserrate, H.C. Vervoort, R.L. Bai, D.J. Newman, S.B. Howell, G. Los, J.T. Mullaney, M.D. Williams, G.R. Pettit, W. Fenical, and E. Hamel Mol. Pharmacol. 63 2003 1273 1280
290. K.C. Nicolaou, M. Bella, D.Y.K. Chen, X.H. Huang, T.T. Ling, and S.A. Snyder Angew. Chem., Int. Ed. 41 2002 3495 3499
291. K.C. Nicolaou, D.Y.K. Chen, X.H. Huang, T.T. Ling, M. Bella, and S.A. Snyder J. Am. Chem. Soc. 126 2004 12888 12896
292. K.C. Nicolaou, P.B. Rao, J.L. Hao, M.V. Reddy, G. Rassias, X.H. Huang, D.Y.K. Chen, and S.A. Snyder Angew. Chem., Int. Ed. 42 2003 1753 1758
293. K.C. Nicolaou, J.L. Hao, M.V. Reddy, P.B. Rao, G. Rassias, S.A. Snyder, X.H. Huang, D.Y.K. Chen, W.E. Brenzovich, N. Giuseppone, P. Giannakakou, and A. O'Brate J. Am. Chem. Soc. 126 2004 12897 12906
294. A.W.G. Burgett, Q.Y. Li, Q. Wei, and P.G. Harran Angew. Chem., Int. Ed. 42 2003 4961 4966
295. F. Lach, and C.J. Moody Tetrahedron Lett. 41 2000 6893 6896
296. F.N. Palmer, F. Lach, C. Poriel, A.G. Pepper, M.C. Bagley, A.M.Z. Slawin, and C.J. Moody Org. Biomol. Chem. 3 2005 3805 3811
297. G. Ni, Z.-F. Shen, Y. Lu, Y.-H. Wang, Y.-B. Tang, R.-Y. Chen, Z.-Y. Hao, and D.-Q. Yu J. Org. Chem. 76 2011 2056 2061
298. Q. Xiao, J.J. Jackson, A. Basak, J.M. Bowler, B.G. Miller, and A. Zakarian Nat. Chem. 5 2013 410 416
299. W.D. Ollis, B.T. Redman, I.O. Sutherland, and K. Jewers J. Chem. Soc., Chem. Commun. 1969 879 880
300. S.-G. Cao, V.H.L. Sng, X.-H. Wu, K.-Y. Sim, B.H.K. Tan, J.T. Pereira, and S.H. Goh Tetrahedron 54 1998 10915 10924
301. S.-G. Cao, X.-H. Wu, K.-Y. Sim, B.K.H. Tan, J.T. Pereira, W.H. Wong, N.F. Hew, and S.H. Goh Tetrahedron Lett. 39 1998 3353 3356
302. X.-H. Wu, B.K.H. Tan, S.-G. Cao, K.-Y. Sim, and S.H. Goh Nat. Prod. Lett. 14 2000 453 458
303. A.J. Quillinan, and F. Scheinmann J. Chem. Soc., Chem. Commun. 1971 966 967
304. K.C. Nicolaou, and L. Jim Angew. Chem., Int. Ed. 40 2001 4264 4268
305. Theodorakis, E.; Batova, A. PCT Int. Appl. WO 2008057604 A2 20080515, 2008.
306. O. Thoison, J. Fahy, V. Dumontet, A. Chiaroni, C. Riche, M.V. Tri, and T. SeÂvenet J. Nat. Prod. 63 2000 441 446
307. E.J. Tisdale, C. Chowdhury, B.G. Vong, H. Li, and E.A. Theodorakis Org. Lett. 4 2002 909 912
308. E.J. Tisdale, B.G. Vong, H. Li, S.H. Kim, C. Chowdhury, and E.A. Theodorakis Tetrahedron 59 2003 6873 6887
309. E.J. Tisdale, I. Slobodov, and E.A. Theodorakis Org. Biomol. Chem. 1 2003 4418 4422
310. E.J. Tisdale, and E.A. Theodorakis Proc. Natl. Acad. Sci. U.S.A. 101 2004 12030 12035
311. E.J. Tisdale, H. Li, B.G. Vong, S.H. Kim, and E.A. Theodorakis Org. Lett. 5 2003 1491 1494
312. Z.-L. Liu, X.-J. Wang, N.-G. Li, H.-P. Sun, J.-X. Wang, and Q.-D. You Tetrahedron 67 2011 4774 4779
313. X. Li, X. Zhang, Z. Yu, X. Liu, Q. You, and Q. Guo J. Chem. Res. 2011 630 633
314. K.C. Majumdar, T. Bhattacharyya, B. Chattopadhyay, and B. Sinha Synthesis 2009 2117 2142
315. K.C. Majumdar, and T. Bhattacharyya J. Indian Chem. Soc. 79 2002 112 121
316. U. Nubbemeyer Top. Curr. Chem. 244 2005 149 213
317. S. Itô, and T. Tsunoda Pure Appl. Chem. 66 1994 2071 2074
318. T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, and S. Itô Tetrahedron Lett. 37 1996 2463 2466
319. B.R. Dunshee, C. Leben, G.W. Keitt, and F.M. Strong J. Am. Chem. Soc. 71 1949 2436 2437
320. M.K.F. Wikstrom, and J.A. Berden Biochim. Biophys. Acta 283 1972 403 420
321. T. Nishii, S. Suzuki, K. Yoshida, K. Arakaki, and T. Tsunoda Tetrahedron Lett. 44 2003 7829 7832
322. T. Tsunoda, T. Nishii, M. Yoshizuka, C. Yamasaki, T. Suzuki, and S. Ito Tetrahedron Lett. 41 2000 7667 7670
323. Y.-S. Lee, J.-W. Jung, S.-H. Kim, J.-K. Jung, S.-M. Paek, N.-J. Kim, D.-J. Chang, J. Lee, and Y.-G. Suh Org. Lett. 12 2010 2040 2043
324. N. Naruse, O. Tenmyo, K. Kawano, K. Tomita, N. Ohgusa, T. Miyaki, M. Konishi, and T. Oki J. Antibiot. 44 1991 733 740
325. A. Randazzo, G. Bifulco, C. Giannini, M. Bucci, C. Debitus, G. Cirino, and L. Gomez-Paloma J. Am. Chem. Soc. 123 2001 10870 10876
326. C.D. Monica, A. Randazzo, G. Bifulco, P. Cimino, M. Aquino, I. Izzo, F.D. Riccardis, and L. Gomez-Paloma Tetrahedron Lett. 43 2002 5707 5710
327. S. Yu, X. Pan, X. Lin, and D. Ma Angew. Chem., Int. Ed. 44 2005 135 138
328. N.J. McCorkindale, J.L. Wright, P.W. Brian, S.M. Clarke, and S.A. Hutchinson Tetrahedron Lett. 1968 727 730
329. M. Kato, M. Kageyama, R. Tanaka, K. Kuwahara, and A. Yoshikoshi J. Org. Chem. 40 1975 1932 1941
330. U. Nubbemeyer J. Org. Chem. 61 1996 3677 3686
331. X. Xiong, and M.C. Pirrung J. Org. Chem. 72 2007 5832 5834
332. A. Sabahi, and J.D. Rainier Arkivoc viii 2010 116 125
333. K.C. Majumdar, S. Ghosh, and M. Ghosh Tetrahedron 59 2003 7251 7271
334. K.C. Majumdar, S. Samanta, B. Chattopadhyay, and N. Pal Curr. Org. Chem. 9 2012 851 872
335. S. Levin, R.R. Nani, and S.E. Reisman J. Am. Chem. Soc. 133 2011 774 776
336. Y. Aoyagi, A. Yamazaki, C. Nakatsugawa, H. Fukaya, K. Takeya, S. Kawauchi, and H. Izumi Org. Lett. 10 2008 4429 4432
337. A. Ortega, J.F. Blount, and P.S. Manchand J. Chem. Soc., Perkin Trans. 1 1982 2505 2508
338. D. Tejedor, G. Méndez-Abt, L. Cotos, and F. García-Tellado Chem. Soc. Rev. 42 2013 458 471
339. A. Nakazaki, and S. Kobayash Synlett 2012 1427 1445