The chemistry of the polycyclic polyprenylated acylphloroglucinols

Angewandte Chemie - International Edition

Volumn 51, Issue 19, 2012, Pages 4536-4561

  Richard, Jean Alexandre ^a   Pouwer, Rebecca H ^a   Chen, David Y K ^b  

^a INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^b Seoul National University   (South Korea)

Author keywords

asymmetric catalysis; biological activity; biomimetic synthesis; natural products; total synthesis

Indexed keywords

ASYMMETRIC CATALYSIS; BIOMIMETIC SYNTHESIS; C-C BOND FORMING REACTION; CURRENT LIMITATION; INTRIGUING MOLECULES; MOLECULAR ARCHITECTURE; NATURAL PRODUCTS; PLAYING FIELDS; SYNTHETIC APPROACH; SYNTHETIC METHODS; TOTAL SYNTHESIS;

BIOACTIVITY; BIOMIMETICS; CATALYSIS; CHEMICAL BONDS;

SYNTHESIS (CHEMICAL);

BIOLOGICAL PRODUCT; PHLOROGLUCINOL; SELENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; PRENYLATION; SYNTHESIS;

BIOLOGICAL AGENTS; CATALYSIS; CYCLIZATION; PHLOROGLUCINOL; PRENYLATION; SELENIUM;

EID: 84860778342     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103873     Document Type: Article

References (214)

1. R. Ciochina, R. B. Grossman, Chem. Rev. 2006, 106, 3963-3986
2. I. P. Singh, S. B. Bharate, Nat. Prod. Rep. 2006, 23, 558-591; for insight regarding their biosynthesis, see
3. Polyprenylated Phloroglucinols and Xanthones, M. Dakanali, E. A. Theodorakis, in Biomimetic Organic Synthesis (Eds.:, E. Poupon, B. Nay,), Wiley-VCH, Weinheim, 2011; for some synthetic aspects, see
4. I. P. Singh, J. Sidana, S. B. Bharate, W. J. Foley, Nat. Prod. Rep. 2010, 27, 393-416; while this Review was under evaluation, another review describing the chemistry of the PPAPs appeared, see
5. J. T. Njardarson, Tetrahedron 2011, 67, 7631-7666.
6. O. Cuesta-Rubio, H. Velez-Castro, B. A. Frontana-Uribe, J. Cárdenas, Phytochemistry 2001, 57, 279-283.
7. For a discussion on the use of PPAPs in the treatment of degenerative diseases, see, L. Verotta, Phytochem. Rev. 2002, 1, 389-407.
8. J. A. Peters, Synthesis 1979, 321-336.
9. E. Butkus, Synlett 2001, 1827-1835.
10. K.-H. Schönwälder, P. Kollat, J. J. Stezowski, F. Effenberger, Chem. Ber. 1984, 117, 3280-3296.
11. S. J. Spessard, B. M. Stoltz, Org. Lett. 2002, 4, 1943-1946.
12. L. Claisen, Ber. Dtsch. Chem. Ges. 1912, 45, 3157-3166; for reviews on the Claisen rearrangement, see
13. F. E. Ziegler, Chem. Rev. 1988, 88, 1423-1452
14. A. M. Martín Castro, Chem. Rev. 2004, 104, 2939-3002
15. The Claisen Rearrangement (Eds.:, M. Hiersemann, U. Nubbemeyer,), Wiley-VCH, Weinheim, 2007.
16. S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968
17. Angew. Chem. Int. Ed. 2003, 42, 1900-1923; for the original protocol with the second-generation Grubbs catalyst, see
18. A. K. Chatterjee, D. P. Sanders, R. H. Grubbs, Org. Lett. 2002, 4, 1939-1942.
19. L. E. McCandlish, J. C. Hanson, G. H. Stout, Acta Crystallogr. Sect. B 1976, 32, 1793-1801
20. for the structural revision of clusianone (7) and its reported anti-HIV activity, see, A. L. Piccinelli, O. Cuesta-Rubio, M. B. Chica, N. Mahmood, B. Pagano, M. Pavone, V. Barone, L. Rastrelli, Tetrahedron 2005, 61, 8206-8211; for its anticancer properties, see
21. C. Ito, M. Itoigawa, Y. Miyamoto, S. Onoda, K. S. Rao, T. Mukainaka, H. Tokuda, H. Nishino, H. Furukawa, J. Nat. Prod. 2003, 66, 206-209.
22. M. R. Garnsey, D. Lim, J. M. Yost, D. M. Coltart, Org. Lett. 2010, 12, 5234-5237.
23. D. Lim, D. M. Coltart, Angew. Chem. 2008, 120, 5285-5288
24. Angew. Chem. Int. Ed. 2008, 47, 5207-5210
25. S. E. Wengryniuk, D. Lim, D. M. Coltart, J. Am. Chem. Soc. 2011, 133, 8714-8720.
26. E. J. Corey, J. W. Suggs, Tetrahedron Lett. 1975, 16, 2647-2650
27. J. H. Babler, M. J. Coghlan, Synth. Commun. 1976, 6, 469-474
28. W. G. Dauben, D. M. Michno, J. Org. Chem. 1977, 42, 682-685.
29. P. Nuhant, M. David, T. Pouplin, B. Delpech, C. Marazano, Org. Lett. 2007, 9, 287-289
30. T. Pouplin, B. Tolon, P. Nuhant, B. Delpech, C. Marazano, Eur. J. Org. Chem. 2007, 5117-5125; for biomimetic considerations from the same research group, see
31. S. Brajeul, B. Delpech, C. Marazano, Tetrahedron Lett. 2007, 48, 5597-5600
32. S. B. Raikar, P. Nuhant, B. Delpech, C. Marazano, Eur. J. Org. Chem. 2008, 1358-1369.
33. V. Rodeschini, N. M. Ahmad, N. S. Simpkins, Org. Lett. 2006, 8, 5283-5285
34. N. M. Ahmad, V. Rodeschini, N. S. Simpkins, S. E. Ward, A. J. Blake, J. Org. Chem. 2007, 72, 4803-4815.
35. V. Rodeschini, N. S. Simpkins, C. Wilson, J. Org. Chem. 2007, 72, 4265-4267.
36. A. J. Blake, G. M. P. Giblin, D. T. Kirk, N. S. Simpkins, C. Wilson, Chem. Commun. 2001, 2668-2669
37. G. M. P. Giblin, D. T. Kirk, L. Mitchell, N. S. Simpkins, Org. Lett. 2003, 5, 1673-1675.
38. Y. Fukuyama, A. Kuwayama, H. Minami, Chem. Pharm. Bull. 1997, 45, 947-949
39. Y. Fukuyama, H. Minami, A. Kuwayama, Phytochemistry 1998, 49, 853-857.
40. N. S. Simpkins, J. D. Taylor, M. D. Weller, C. J. Hayes, Synlett 2010, 639-643. Isolation
41. J. Lokvam, J. F. Braddock, P. B. Reichardt, T. P. Clausen, Phytochemistry 2000, 55, 29-34
42. O. Cuesta-Rubio, H. Velez-Castro, B. A. Frontana-Uribe, J. Cárdenas, Phytochemistry 2001, 57, 279-283.
43. J. Qi, J. A. Porco, Jr., J. Am. Chem. Soc. 2007, 129, 12682-12683.
44. M. Mondal, V. G. Puranik, N. P. Argade, J. Org. Chem. 2007, 72, 2068-2076.
45. G. Hughes, M. Lautens, C. Wen, Org. Lett. 2000, 2, 107-110.
46. J. Qi, A. B. Beeler, Q. Zhang, J. A. Porco, Jr., J. Am. Chem. Soc. 2010, 132, 13642-13644; for the isolation of hyperibone K (8) and its moderate cytotoxicity; see
47. N. Tanaka, Y. Takaishi, Y. Shikishima, Y. Nakanishi, K. Bastow, K.-H. Lee, G. Honda, M. Ito, Y. Takeda, O. K. Kodzhimatov, O. Ashurmetov, J. Nat. Prod. 2004, 67, 1870-1875.
48. M. J. O'Donnell, Acc. Chem. Res. 2004, 37, 506-517
49. B. Lygo, B. I. Andrews, Acc. Chem. Res. 2004, 37, 518-525
50. P. V. Ramachandran, S. Madhi, L. Bland-Berry, M. V. Ram Reddy, M. J. O'Donnell, J. Am. Chem. Soc. 2005, 127, 13450-13451.
51. S.-S. Jew, B.-S. Jeong, M.-S. Yoo, H. Huh, H.-G. Park, Chem. Commun. 2001, 1244-1245
52. S.-S. Jew, J.-H. Lee, B.-S. Jeong, M.-S. Yoo, M.-J. Kim, Y.-J. Lee, J. Lee, S.-H. Choi, K. Lee, M. S. Lah, H.-G. Park, Angew. Chem. 2005, 117, 1407-1409
53. Angew. Chem. Int. Ed. 2005, 44, 1383-1385
54. M. B. Andrus, M. A. Christiansen, E. J. Hicken, M. J. Gainer, K. D. Bedke, K. C. Harper, S. R. Mikkelson, D. S. Dodson, D. T. Harris, Org. Lett. 2007, 9, 4865-4868
55. J.-H. Lee, M.-S. Yoo, J.-H. Jung, S.-S. Jew, H.-G. Park, B.-S. Jeong, Tetrahedron 2007, 63, 7906-7915.
56. Y. Quesnel, L. Toupet, L. Duhamel, P. Duhamel, J.-M. Poirier, Tetrahedron: Asymmetry 1999, 10, 1015-1018
57. P. R. Carlier, C. W. S. Lo, M. M. C. Lo, N. C. Wan, I. D. Williams, Org. Lett. 2000, 2, 2443-2445.
58. M. Noji, Y. Konno, K. Ishii, J. Org. Chem. 2007, 72, 5161-5167.
59. Q. Zhang, B. Mitasev, J. Qi, J. A. Porco, Jr., J. Am. Chem. Soc. 2010, 132, 14212-14215. Isolation
60. G. E. Henry, H. Jacobs, C. M. Sean Carrington, S. McLean, W. F. Reynolds, Tetrahedron Lett. 1996, 37, 8663-8666; antitumoral activity
61. D. Díaz-Carballo, S. Malak, W. Bardenheuer, M. Freistuehler, H. P. Reusch, Bioorg. Med. Chem. 2008, 16, 9635-9643; biosynthetic origin
62. C. M. A. de Oliveira, A. L. M. Porto, V. Bittrich, A. J. Marsaioli, Phytochemistry 1999, 50, 1073-1079
63. L.-H. Hu, K.-Y. Sim, Tetrahedron 2000, 56, 1379-1386.
64. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, Y. Kamiya, J. Am. Chem. Soc. 1989, 111, 4392-4398.
65. T. W. Bentley, G. Llewellyn, Z. H. Ryu, J. Org. Chem. 1998, 63, 4654-4659; for a review on fluorinated solvents, see
66. I. A. Shuklov, N. V. Dubrovina, A. Börner, Synthesis 2007, 2925-2943.
67. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170
68. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163
69. L. F. Tietze, Chem. Rev. 1996, 96, 115-136
70. L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006
71. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344
72. Angew. Chem. Int. Ed. 2006, 45, 7134-7186
73. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993-3009.
74. N. S. Simpkins, M. D. Weller, Tetrahedron Lett. 2010, 51, 4823-4826; the core of the ialibinones was also achieved through a ring-closing metathesis strategy, see
75. A. Srikrishna, B. Beeraiah, V. Gowri, Tetrahedron 2009, 65, 2649-2654; for the isolation of ialibinones A (5) and B (102) and their reported antibacterial activity, see
76. K. Winkelmann, J. Heilmann, O. Zerbe, T. Rali, O. Sticher, J. Nat. Prod. 2000, 63, 104-108.
77. B. McCarthy Cole, L. Han, B. B. Snider, J. Org. Chem. 1996, 61, 7832-7847
78. for a review, see, B. B. Snider, Chem. Rev. 1996, 96, 339-364
79. for some insight about the mechanism, see, B. B. Snider, Tetrahedron 2009, 65, 10738-10744.
80. J. H. George, M. D. Hesse, J. E. Baldwin, R. M. Adlington, Org. Lett. 2010, 12, 3532-3535.
81. For a review on the applications of TEMPO in synthesis, see, T. Vogler, A. Studer, Synthesis 2008, 1979-1993.
82. For the isolation of hyperguinone B (104), its cytotoxicity, and antibacterial activity, see, K. Winkelmann, J. Heilmann, O. Zerbe, T. Rali, O. Sticher, J. Nat. Prod. 2001, 64, 701-706.
83. C. Tsukano, D. R. Siegel, S. J. Danishefsky, Angew. Chem. 2007, 119, 8996-9000
84. Angew. Chem. Int. Ed. 2007, 46, 8840-8844.
85. T. Satoh, M. Ikeda, M. Miura, M. Nomura, J. Org. Chem. 1997, 62, 4877-4879.
86. G. E. Keck, J. B. Yates, J. Am. Chem. Soc. 1982, 104, 5829-5831.
87. For a review on the halogen-magnesium exchange, see, P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. 2003, 115, 4438-4456
88. Angew. Chem. Int. Ed. 2003, 42, 4302-4320.
89. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
90. D. R. Siegel, S. J. Danishefsky, J. Am. Chem. Soc. 2006, 128, 1048-1049.
91. H. Usuda, M. Kanai, M. Shibasaki, Org. Lett. 2002, 4, 859-862
92. H. Usuda, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2002, 43, 3621-3624
93. Y. Shimizu, A. Kuramochi, H. Usuda, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2007, 48, 4173-4177.
94. A. Kuramochi, H. Usuda, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 14200-14201.
95. J. C. Martin, R. J. Arhart, J. Am. Chem. Soc. 1971, 93, 4327-4329
96. R. J. Arhart, J. C. Martin, J. Am. Chem. Soc. 1972, 94, 5003-5010.
97. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547
98. P. Dupau, R. Epple, A. A. Thomas, V. V. Fokin, K. B. Sharpless, Adv. Synth. Catal. 2002, 344, 421-433; Nobel lecture
99. K. B. Sharpless, Angew. Chem. 2002, 114, 2126-2135
100. Angew. Chem. Int. Ed. 2002, 41, 2024-2032.
101. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601
102. Angew. Chem. Int. Ed. 2005, 44, 4490-4527
103. A. Gradillas, J. Pérez-Castells, Angew. Chem. 2006, 118, 6232-6247
104. Angew. Chem. Int. Ed. 2006, 45, 6086-6101.
105. S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179.
106. J. Tsuji, Synthesis 1984, 369-384
107. R. Jira, Angew. Chem. 2009, 121, 9196-9199
108. Angew. Chem. Int. Ed. 2009, 48, 9034-9037.
109. M. Imai, A. Hagihara, H. Kawasaki, K. Manabe, K. Koga, J. Am. Chem. Soc. 1994, 116, 8829-8830.
110. N. S. Bystrov, B. K. Chernov, V. N. Dobrynin, M. N. Kolosov, Tetrahedron Lett. 1975, 16, 2791-2794; proposed biosynthesis
111. P. Adam, D. Arigoni, A. Bacher, W. Eisenreich, J. Med. Chem. 2002, 45, 4786-4793; for the antidepressant mechanism of Hypericum perforatum, see
112. T. Mennini, M. Gobbi, Life Sci. 2004, 75, 1021-1027; for a review on the chemistry, pharmacology, and clinical properties of St.John's wort (Hypericum perforatum) and hyperforin (3), see
113. J. Barnes, L. A. Anderson, J. D. Phillipson, J. Pharm. Pharmacol. 2001, 53, 583-600
114. C. Quiney, C. Billard, C. Salanoubat, J. D. Fourneron, J. P. Kolb, Leukemia 2006, 20, 1519-1525
115. M. A. Medina, B. Martínez-Poveda, M. I. Amores-Sánchez, A. R. Quesada, Life Sci. 2006, 79, 105-111; for a highlight on the history and properties of hyperforin (3), see
116. L. Beerhues, Phytochemistry 2006, 67, 2201-2207.
117. Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai, M. Shibasaki, Angew. Chem. 2010, 122, 1121-1124
118. Angew. Chem. Int. Ed. 2010, 49, 1103-1106
119. Y. Shimizu, S.-L. Shi, H. Usuda, M. Kanai, M. Shibasaki, Tetrahedron 2010, 66, 6569-6584.
120. H. Usuda, A. Kuramochi, M. Kanai, M. Shibasaki, Org. Lett. 2004, 6, 4387-4390.
121. W. P. Griffith, S. V. Ley, G. P. Whitcombe, A. D. White, J. Chem. Soc. Chem. Commun. 1987, 1625-1627; for a review, see
122. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639-666.
123. Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013
124. R. C. Larock, T. R. Hightower, G. A. Kraus, P. Hahn, D. Zheng, Tetrahedron Lett. 1995, 36, 2423-2426.
125. K. S. Feldman, M. D. Fodor, J. Am. Chem. Soc. 2008, 130, 14964-14965; for selected reviews on the Pummerer reaction, see
126. S. K. Bur, A. Padwa, Chem. Rev. 2004, 104, 2401-2432
127. K. S. Feldman, Tetrahedron 2006, 62, 5003-5034
128. L. H. S. Smith, S. C. Coote, H. F. Sneddon, D. J. Procter, Angew. Chem. 2010, 122, 5968-5980
129. Angew. Chem. Int. Ed. 2010, 49, 5832-5844.
130. >For the thermal rearrangement of xanthates to dithiolcarbonates, see, T. Taguchi, Y. Kawazoe, M. Nakao, Tetrahedron Lett. 1963, 4, 131-135.
131. K. C. Nicolaou, J. A. Pfefferkorn, S. Kim, H. X. Wei, J. Am. Chem. Soc. 1999, 121, 4724-4725
132. K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, S. Kim, J. Kessabi, Org. Lett. 1999, 1, 807-810.
133. L. A. Decosterd, H. Stoeckli-Evans, J.-C. Chapuis, J. D. Msonthi, B. Sordat, K. Hostettmann, Helv. Chim. Acta 1989, 72, 464-471.
134. D. G. J. Young, D. Zeng, J. Org. Chem. 2002, 67, 3134-3137; for some early allene-nitrile oxide cycloadditions, see
135. G. Zecchi, J. Org. Chem. 1979, 44, 2796-2798
136. L. Bruche, M. L. Gelmi, G. Zecchi, J. Org. Chem. 1985, 50, 3206-3208; for a review on intramolecular 1,3-dipolar cycloaddition reactions in targeted synthesis, see
137. V. Nair, T. D. Suja, Tetrahedron 2007, 63, 12247-12275.
138. H. Gilman, R. G. Jones, L. A. Woods, J. Org. Chem. 1952, 17, 1630-1634
139. J. P. Kutney, A. H. Ratcliffe, Synth. Commun. 1975, 5, 47-52.
140. A. J. Mancuso, D. Swern, Synthesis 1981, 165-185.
141. T. Mukaiyama, K. Banno, K. Narasaka, J. Am. Chem. Soc. 1974, 96, 7503-7509.
142. T. Mukaiyama, T. Hoshino, J. Am. Chem. Soc. 1960, 82, 5339-5342.
143. R. Ciochina, R. B. Grossman, Org. Lett. 2003, 5, 4619-4621.
144. J. D. White, R. W. Skeean, G. L. Trammell, J. Org. Chem. 1985, 50, 1939-1948.
145. M. G. Moloney, J. T. Pinhey, E. G. Roche, J. Chem. Soc. Perkin Trans. 1 1989, 333-341.
146. S. Hosokawa, M. Isobe, Tetrahedron Lett. 1998, 39, 2609-2612
147. K. Kira, H. Tanda, A. Hamajima, T. Baba, S. Takai, M. Isobe, Tetrahedron 2002, 58, 6485-6492.
148. A. Klein, M. Miesch, Tetrahedron Lett. 2003, 44, 4483-4485.
149. K. C. Nicolaou, G. E. A. Carenzi, V. Jeso, Angew. Chem. 2005, 117, 3963-3967
150. Angew. Chem. Int. Ed. 2005, 44, 3895-3899; isolation
151. J. Wu, X.-F. Cheng, L. J. Harrison, S.-H. Goh, K.-Y. Sim, Tetrahedron Lett. 2004, 45, 9657-9659.
152. P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206
153. S. Arns, L. Barriault, Chem. Commun. 2007, 2211-2221.
154. R. M. A. Lavigne, M. Riou, M. Girardin, L. Morency, L. Barriault, Org. Lett. 2005, 7, 5921-5923.
155. M. H. Hopkins, L. E. Overman, J. Am. Chem. Soc. 1987, 109, 4748-4749; for an account on the Prins/pinacol reaction in total synthesis, see
156. L. E. Overman, L. D. Pennington, J. Org. Chem. 2003, 68, 7143-7157.
157. N. M. Ahmad, V. Rodeschini, N. S. Simpkins, S. E. Ward, C. Wilson, Org. Biomol. Chem. 2007, 5, 1924-1934.
158. K. D. Sears, R. L. Casebier, H. L. Hergert, G. H. Stout, L. E. McCandlish, J. Org. Chem. 1974, 39, 3244-3247.
159. R. K. Boeckman, Jr., A. Arvanitis, M. E. Voss, J. Am. Chem. Soc. 1989, 111, 2737-2739.
160. G. A. Kraus, I. Jeon, Tetrahedron Lett. 2008, 49, 286-288; for a radical cyclization approach for the preparation of PPAPs, see
161. G. A. Kraus, T. H. Nguyen, I. Jeon, Tetrahedron Lett. 2003, 44, 659-661
162. G. A. Kraus, E. Dneprovskaia, T. H. Nguyen, I. Jeon, Tetrahedron 2003, 59, 8975-8978.
163. A. Durant, J. L. Delplancke, V. Libert, J. Reisse, Eur. J. Org. Chem. 1999, 2845-2851.
164. A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105
165. Angew. Chem. Int. Ed. 2006, 45, 7896-7936
166. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
167. A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519
168. Angew. Chem. Int. Ed. 2007, 46, 3410-3449
169. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403
170. E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun. 2007, 333-346
171. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350; for a review on gold catalysis in total synthesis, see
172. A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766-1775.
173. F. Barabe', G. Be'tournay, G. Bellavance, L. Barriault, Org. Lett. 2009, 11, 4236-4238.
174. B. Mitasev, J. A. Porco, Jr., Org. Lett. 2009, 11, 2285-2288.
175. For a review on transannulation reactions in natural products synthesis, see, P. A. Clarke, A. T. Reeder, J. Winn, Synthesis 2009, 691-709.
176. Y. Kuninobu, J. Morita, M. Nishi, A. Kawata, K. Takai, Org. Lett. 2009, 11, 2535-2537.
177. Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc. 2006, 128, 11368-11369.
178. H. Zhang, S.-P. Yang, C.-Q. Fan, J. Ding, J.-M. Yue, J. Nat. Prod. 2006, 69, 553-557.
179. I. N. Michaelides, B. Darses, D. J. Dixon, Org. Lett. 2011, 13, 664-667.
180. E. A. Couladouros, M. Dakanali, K. D. Demadis, V. P. Vidali, Org. Lett. 2009, 11, 4430-4433.
181. R. Takagi, T. Nerio, Y. Miwa, S. Matsumura, K. Ohkata, Tetrahedron Lett. 2004, 45, 7401-7405
182. R. Takagi, Y. Miwa, S. Matsumura, K. Ohkata, J. Org. Chem. 2005, 70, 8587-8589
183. R. Takagi, Y. Miwa, T. Nerio, Y. Inoue, S. Matsumura, K. Ohkata, Org. Biomol. Chem. 2007, 5, 286-300.
184. R. Takagi, Y. Inoue, K. Ohkata, J. Org. Chem. 2008, 73, 9320-9325.
185. M. Abe, M. Nakada, Tetrahedron Lett. 2006, 47, 6347-6351
186. M. Abe, M. Nakada, Tetrahedron Lett. 2007, 48, 4873-4877
187. M. Abe, A. Saito, M. Nakada, Tetrahedron Lett. 2010, 51, 1298-1302.
188. G. Mehta, M. K. Bera, Tetrahedron Lett. 2006, 47, 689-692
189. G. Mehta, M. K. Bera, S. Chatterjee, Tetrahedron Lett. 2008, 49, 1121-1124
190. G. Mehta, M. K. Bera, Tetrahedron Lett. 2008, 49, 1417-1420
191. G. Mehta, M. K. Bera, Tetrahedron Lett. 2009, 50, 3519-3522.
192. G. Mehta, T. Dhanbal, M. K. Bera, Tetrahedron Lett. 2010, 51, 5302-5305.
193. A. S. Kende, B. Roth, P. J. Sanfilippo, J. Am. Chem. Soc. 1982, 104, 1784-1785.
194. G. Mehta, M. K. Bera, Tetrahedron Lett. 2004, 45, 1113-1116.
195. C. Uyeda, A. R. Rötheli, E. N. Jacobsen, Angew. Chem. 2010, 122, 9947-9950
196. Angew. Chem. Int. Ed. 2010, 49, 9753-9756.
197. C. Uyeda, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 9228-9229.
198. S. F. Martin, Tetrahedron 1980, 36, 419-460
199. K. Fuji, Chem. Rev. 1993, 93, 2037-2066
200. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 2092-2118
201. Angew. Chem. Int. Ed. 1998, 37, 388-401
202. I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105-10146
203. E. A. Peterson, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 11943-11948
204. J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473-1482
205. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis (Eds.:, J. Christoffers, A. Baro,), Wiley, Weinheim, 2005
206. B. M. Trost, C. Jiang, Synthesis 2006, 369-396.
207. N. A. McGrath, J. R. Binner, G. Markopoulos, M. Brichacek, J. T. Njardarson, Chem. Commun. 2011, 47, 209-211.
208. L. Verotta, G. Appendino, J. Jakupovic, E. Bombardelli, J. Nat. Prod. 2000, 63, 412-415
209. L. Verotta, G. Appendino, E. Belloro, F. Bianchi, O. Sterner, M. Lovati, E. Bombardelli, J. Nat. Prod. 2002, 65, 433-438
210. M. Gartner, T. Müller, J. C. Simon, A. Giannis, J. P. Sleeman, ChemBioChem 2005, 6, 171-177
211. L. Verotta, G. Appendino, E. Bombardelli, R. Brun, Bioorg. Med. Chem. Lett. 2007, 17, 1544-1548
212. C. Gey, S. Kyrylenko, L. Hennig, L.-H. D. Nguyen, A. Büttner, H. D. Pham, A. Giannis, Angew. Chem. 2007, 119, 5311-5314
213. Angew. Chem. Int. Ed. 2007, 46, 5219-5222
214. M. Rothley, A. Schmid, W. Thiele, V. Schacht, D. Plaumann, M. Gartner, A. Yektaoglu, F. Bruyère, A. Noël, A. Giannis, J. P. Sleeman, Int. J. Cancer 2009, 125, 34-42.