Chemical synthesis of the cardiotonic steroid glycosides and related natural products

Chemistry - A European Journal

Volumn 18, Issue 11, 2012, Pages 3092-3120

  Heasley, Brian ^a  

^a SCYNEXIS Inc   (United States)

Author keywords

digitoxin; medicinal chemistry; ouabain; semisynthesis; steroids; total synthesis

Indexed keywords

DIGITOXIN; MEDICINAL CHEMISTRY; OUABAIN; SEMISYNTHESIS; STEROIDS; TOTAL SYNTHESIS;

LIPIDS; SODIUM; SUGARS;

GLYCOSIDES;

BIOLOGICAL PRODUCT; CARDIAC GLYCOSIDE; DIGITALIS; DIGITALIS GLYCOSIDE;

CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; REVIEW; SYNTHESIS;

BIOLOGICAL AGENTS; CARDIAC GLYCOSIDES; DIGITALIS; DIGITALIS GLYCOSIDES; HUMANS; MOLECULAR STRUCTURE;

EID: 84857823601     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103733     Document Type: Review

References (177)

1. A. J. Levi, M. R. Boyett, C. O. Lee, Prog. Biophys. Mol. Biol. 1994, 62, 1-54
2. C. P. Melero, M. Medarde, A. San Feliciano, Molecules 2000, 5, 51-81
3. R. I. Dmitrieva, P. A. Doris, Exp. Biol. Med. 2002, 227, 561-569
4. W. Schoner, Eur. J. Biochem. 2002, 269, 2440-2448
5. H. P. Albrecht, K.-H. Geiss, Cardiac Glycosides and Synthetic Cardiotonic Drugs: Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005
6. A. Y. Bagrov, J. I. Shapiro, O. V. Fedorova, Pharmacol. Rev. 2009, 61, 9-38.
7. S. M. Keenan, R. K. DeLisle, W. J. Welsh, S. Paula, W. J. Ball, Jr., J. Mol. Graph. Model. 2005, 23, 465-475
8. F. Cornelius, Y. A. Mahmmoud, Biochemistry 2009, 48, 10056-10065
9. Z. Li, Z. Xie, Eur. J. Physiol. 2009, 457, 635-644.
10. N. Reyes, D. C. Gadsby, Nature 2006, 443, 470-474.
11. T. Drakenberg, P. Brodelius, D. D. McIntyre, H. J. Vogel, Can. J. Chem. 1990, 68, 272-277
12. A. Kawamura, L. M. Abrell, F. Maggiali, N. Berova, K. Nakanishi, J. Labutti, S. Magil, G. T. Haupert, Jr., J. M. Hamlyn, Biochemistry 2001, 40, 5835-5844.
13. G. P. Moss, Pure Appl. Chem. 1989, 61, 1783-1822. For a recent review on the enantioselective synthesis of steroids, see
14. A.-S. Chapelon, D. Moraleda, R. Rodriguez, C. Ollivier, M. Santelli, Tetrahedron 2007, 63, 11511-11616.
15. K. Wiesner, T. Y. R. Tsai, Pure Appl. Chem. 1986, 58, 799-810.
16. M. M. Kabat, J. Org. Chem. 1995, 60, 1823-1827
17. J. Wicha, M. M. Kabat, J. Chem. Soc. Perkin Trans. 1 1985, 1601.
18. P. S. Steyn, F. R. van Heerden, Nat. Prod. Rep. 1998, 15, 397-413
19. H. Gao, R. Popescu, B. Kopp, Z. Wang, Nat. Prod. Rep. 2011, 28, 953-969.
20. B. Heasley, Eur. J. Org. Chem. 2011, 19-46.
21. E. Van Quaquebeke, G. Simon, A. Andre, J. Dewelle, M. E. Yazidi, F. Bruyneel, J. Tuti, O. Nacoulma, P. Guissou, C. Decaestecker, J.-C. Braekman, R. Kiss, F. Darro, J. Med. Chem. 2005, 48, 849-856
22. T. Mijatovic, F. Lefranc, E. V. Quaquebeke, F. V. Vynckt, F. Darro, R. Kiss, Drug Dev. Res. 2007, 68, 164-173
23. S. Piacente, M. Masullo, N. D. Neve, J. Dewelle, A. Hamed, R. Kiss, T. Mijatovic, J. Nat. Prod. 2009, 72, 1087-1091.
24. T. Mijatovic, E. V. Quaquebeke, B. Delest, O. Debeir, F. Darro, R. Kiss, Biochim. Biophys. Acta 2007, 1776, 32-57. For a related example of an antiproliferative cardenolide, see
25. S. Cao, P. J. Brodie, J. S. Miller, F. Ratovoson, M. W. Callmander, S. Randrianasolo, E. Rakotobe, V. E. Rasamison, E. M. Suh, K. TenDyke, D. G. I. Kingston, J. Nat. Prod. 2007, 70, 1064-1067.
26. W. Schoner, N. Bauer, J. Muller-Ehmsen, U. Kramer, N. Hambarchian, R. Schwinger, H. Moeller, H. Kost, C. Weitkamp, T. Schweitzer, U. Kirch, H. Neu, E.-G. Grunbaum, Ann. N. Y. Acad. Sci. 2003, 986, 678-684. An endogenous cardiotonic steroid found in human plasma has properties similar to ouabain but is not structurally identical to ouabain
27. [1d, 12a] For a bioinoformatics-based analysis of the putative mammalian biosynthetic pathway by which a ouabain-like compound (OLC) is synthesized from cholesterol, see
28. J. R. Murrell, J. D. Randall, J. Rosoff, J.-l. Zhao, R. V. Jensen, S. R. Gullans, G. T. Haupert, Circulation 2005, 112, 1301-1308.
29. O. Aizman, P. Uhlen, M. Lai, H. Brismar, A. Aperia, Proc. Natl. Acad. Sci. USA 2001, 98, 13420-13424
30. G. Scheiner-Bobis, W. Schoner, Nat. Med. 2001, 7, 1288-1289. For a recent identification of digoxin (4) as a specific inhibitor of transcriptional activity, see
31. J. R. Huh, M. W. L. Leung, P. Huang, D. A. Ryan, M. R. Krout, R. R. V. Malapaka, J. Chow, N. Manel, M. Ciofani, S. V. Kim, A. Cuesta, F. R. Santori, J. J. lafaille, H. E. Xu, D. Y. Gin, F. Rastinejad, D. R. Littman, Nature 2011, 472, 486-490.
32. L. Quadri, G. Bianchi, A. Cerri, G. Fedrizzi, P. Ferrari, M. Gobbini, P. Melloni, S. Sputore, M. Torri, J. Med. Chem. 1997, 40, 1561-1564
33. P. Ferrari, M. Ferrandi, G. Valentini, G. Bianchi, Am. J. Physiol. Regul. Integr. Comp. Physiol. 2006, 290, R 529 -R 535.
34. H.-Y. Tian, L. Wang, X.-Q. Zhang, Y. Wang, D.-M. Zhang, R.-W. Jiang, Z. Liu, J.-S. Liu, Y.-L. Li, W.-C. Ye, Chem. Eur. J. 2010, 16, 10989-10993, and references therein.
35. T. Yamagishi, M. Haruna, X.-Z. Yan, J.-J. Chang, K.-H. Lee, J. Nat. Prod. 1989, 52, 1071-1079.
36. T. Eisner, D. F. Wiemer, L. W. Haynes, J. Meinwald, Proc. Natl. Acad. Sci. USA 1978, 75, 905-908
37. J. Meinwald, D. F. Wiemer, T. Eisner, J. Am. Chem. Soc. 1979, 101, 3055-3060.
38. R. Tschesche, Proc. R. Soc. London Ser. B 1972, 180, 187-202.
39. V. Ojetti, A. Migneco, F. Bononi, A. De Lorenzo, N. G. Silveri, Eur. Rev. Med. Pharmacol. Sci. 2005, 9, 241-246.
40. Digitalis poisoning has been referenced extensively in popular culture. For example, the toxicity of Lily of the Valley featured prominently in the plot of the AMC television series Breaking Bad when Walter White, a morally unscrupulous yet inexplicably endearing organic chemist, used the poisonous garden plant to commit a dastardly poisoning. This event served as a significant plot point in the final two episodes of season 4. More than 30 cardiotonic steroid glycosides (e.g., convallatoxin) have been isolated from Lily of the Valley:, D. G. Barceloux, Digitalis-Containing Flowers (Foxglove, Lily of the Valley), in Medical Toxicology of Natural Substances: Foods, Fungi, Medicinal Herbs, Plants, and Venomous Animals, Wiley, Hoboken, NJ (USA), 2008.
41. P. W. Erhardt, J. Med. Chem. 1987, 30, 231-237
42. K. R. H. Repke, R. Megges, J. Weiland, R. Schon, Angew. Chem. 1995, 107, 308-321
43. Angew. Chem. Int. Ed. Engl. 1995, 34, 282-294.
44. J. W. Daly, J. Nat. Prod. 1998, 61, 162-172
45. J. W. Daly, T. F. Spande, H. M. Garraffo, J. Nat. Prod. 2005, 68, 1556-1575, and references therein.
46. M. Kurosu, Y. Kishi, J. Synth. Org. Chem. Jpn. 2004, 62, 1205-1217.
47. X. Zhu, R. R. Schmidt, Angew. Chem. 2009, 121, 1932
48. Angew. Chem. Int. Ed. 2009, 48, 1900
49. R. R. Schmidt, Angew. Chem. 1986, 98, 213-236
50. Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235
51. K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531. For reviews on the construction of 2-deoxyglycosidic linkages, see
52. C. H. Marzabadi, R. W. Frank, Tetrahedron 2000, 56, 8385
53. D. Hou, T. L. Lowary, Carbohydr. Res. 2009, 344, 1911. Partial synthesis of digitoxin (3) by means of stereoselective β-glycosidation of digitoxose and digitoxigenin
54. H. Jin, T. Y. R. Tsai, K. Wiesner, Can. J. Chem. 1983, 61, 2442-2444
55. T. Y. R. Tsai, H. Jin, K. Wiesner, Can. J. Chem. 1984, 62, 1403-1405
56. K. Wiesner, T. Y. R. Tsai, H. Jin, Helv. Chim. Acta 1985, 68, 300-314
57. M. Zhou, G. A. O'Doherty, J. Org. Chem. 2007, 72, 2485-2493
58. H.-Y. L. Wang, B. Wu, Q. Zhang, S.-W. Kang, Y. Rojanasakul, G. A. O'Doherty, ACS Med. Chem. Lett. 2011, 2, 259-263
59. F. E. McDonald, K. S. Reddy, Angew. Chem. 2001, 113, 3765-3767
60. Angew. Chem. Int. Ed. 2001, 40, 3653-3655
61. F. E. McDonald, C. B. Connolly, M. M. Gleason, T. B. Towne, K. D. Treiber, J. Org. Chem. 1993, 58, 6952-6953
62. Y. Ma, Z. Li, H. Shi, J. Zhang, B. Yu, J. Org. Chem. 2011, 76, 9748-9756; for related leading references describing the assembly of 2- deoxyoligosaccharides and/or cardiotonic steroid genin glycosylation, see
63. J. M. Langenhan, N. R. Peters, I. A. Guzei, F. M. Hoffmann, J. S. Thorson, Proc. Natl. Acad. Sci. USA 2005, 102, 12305-12310
64. K. Yoshida, T. Furuta, T. Kawabata, Tetrahedron Lett. 2010, 51, 4830-4832
65. X. Yang, B. Fu, B. Yu, J. Am. Chem. Soc. 2011, 133, 12433-12435.
66. N. Danieli, Y. Mazur, F. Sondheimer, J. Am. Chem. Soc. 1962, 84, 875-876.
67. J. D. Fell, C. H. Heathcock, J. Org. Chem. 2002, 67, 4742-4746.
68. R. E. Marker, E. Rohrmann, J. Am. Chem. Soc. 1939, 61, 3592-3593
69. R. E. Marker, Chem. Eng. News 1949, 27, 3348-3349
70. P. A. Lehmann, A. Bolivar, R. Quintero, J. Chem. Educ. 1973, 50, 195-199.
71. H. J. Bestmann, D. Sandmeier, Chem. Ber. 1980, 113, 274.
72. R. Marini-Bettolo, P. Flecker, T. Y. R. Tsai, K. Wiesner, Can. J. Chem. 1981, 59, 1403-1404
73. K. Wiesner, T. Y. R. Tsai, Natural Products Research Center, University of New Brunswick, Fredericton, New Brunswick (Canada), Patent Appl. No. 80,004, 1979.
74. A. R. Daniewski, P. S. White, Z. Valenta, Can. J. Chem. 1979, 57, 1397-1398
75. A. R. Daniewski, M. M. Kabat, M. Masnyk, J. Wicha, W. Wojciechowska, J. Org. Chem. 1988, 53, 4855-4858.
76. B. List, Acc. Chem. Res. 2004, 37, 548-557
77. H. Zhu, F. R. Clemente, K. N. Houk, M. P. Meyer, J. Am. Chem. Soc. 2009, 131, 1632-1633.
78. D. H. R. Barton, G. Bashiardes, J.-L. Fourrey, Tetrahedron Lett. 1983, 24, 1605-1608.
79. E. Vedejs, D. A. Engler, J. E. Telschow, J. Org. Chem. 1978, 43, 188.
80. G. Stork, F. West, H. Y. Lee, R. C. A. Isaacs, S. Manabe, J. Am. Chem. Soc. 1996, 118, 10660-10661.
81. G. Stork, N. H. Baine, J. Am. Chem. Soc. 1982, 104, 2321.
82. M. Honma, T. Sawada, Y. Fujisawa, M. Utsugi, H. Watanabe, A. Umino, T. Matsumura, T. Hagihara, M. Takano, M. Nakada, J. Am. Chem. Soc. 2003, 125, 2860-2861
83. M. Honma, M. Nakada, Tetrahedron Lett. 2007, 48, 1541-1544.
84. M. Ochiai, T. Ito, H. Takahashi, A. Nakanishi, M. Toyonari, T. Sueda, S. Goto, M. Shiro, J. Am. Chem. Soc. 1996, 118, 7716-7730.
85. B. Heasley, Eur. J. Org. Chem. 2009, 1477-1489.
86. D. W. Brooks, H. Mazdiyasni, P. G. Grothaus, J. Org. Chem. 1987, 52, 3223-3232
87. H. Watanabe, M. Iwamoto, M. Nakada, J. Org. Chem. 2005, 70, 4652-4658.
88. M. R. Kernan, D. J. Faulkner, J. Org. Chem. 1988, 53, 2773-2776.
89. M. E. Jung, P. Davidov, Angew. Chem. 2002, 114, 4299-4302
90. Angew. Chem. Int. Ed. 2002, 41, 4125-4128
91. M. E. Jung, H. V. Chu, Org. Lett. 2008, 10, 3647-3649
92. M. E. Jung, D. Yoo, Org. Lett. 2011, 13, 2698-2701.
93. H. Nemoto, N. Matsuhashi, M. Imaizumi, M. Nagai, K. Fukumoto, J. Org. Chem. 1990, 55, 5625-5631.
94. G. Stork, E. W. Logusch, J. Am. Chem. Soc. 1980, 102, 1218-1219
95. G. Stork, E. W. Logusch, J. Am. Chem. Soc. 1980, 102, 1219-1220.
96. H. Meier, K.-P. Zeller, Angew. Chem. 1977, 89, 876-890
97. Angew. Chem. Int. Ed. Engl. 1977, 16, 835-851. For a recent application of pyrazoline thermolysis to the synthesis of μ-opioid receptor antagonists, see
98. S. F. McHardy, S. D. Heck, S. Guediche, M. Kalman, M. P. Allen, M. Tu, D. K. Bryce, A. W. Schmidt, M. Vanase-Frawley, E. Callegari, S. Doran, N. J. Grahame, S. McLean, S. Liras, Med. Chem. Commun. 2011, 2, 1001-1005.
99. L. E. Overman, P. V. Rucker, Tetrahedron Lett. 1998, 39, 4643-4646.
100. S. Laschat, F. Narjes, L. E. Overman, Tetrahedron 1994, 50, 347-358
101. W. Deng, M. S. Jensen, L. E. Overman, P. V. Rucker, J.-P. Vionnet, J. Org. Chem. 1996, 61, 6760-6761.
102. J. Hynes, Jr., L. E. Overman, T. Nasser, P. V. Rucker, Tetrahedron Lett. 1998, 39, 4647-4650.
103. J.-F. Lavallée, P. Deslongchamps, Tetrahedron Lett. 1988, 29, 6033-6036.
104. J.-F. Lavallée, P. Deslongchamps, Tetrahedron Lett. 1988, 29, 5117-5118
105. D. Petrovic, R. Bruckner, Org. Lett. 2011, 13, 6524-6527.
106. D. Chapdelaine, J. Belzile, P. Deslongchamps, J. Org. Chem. 2002, 67, 5669-5672
107. Z. Yang, D. Shannon, V.-L. Truong, P. Deslongchamps, Org. Lett. 2002, 4, 4693-4696.
108. S. Trudeau, P. Deslongchamps, J. Org. Chem. 2004, 69, 832-838
109. H. Zhang, M. S. Reddy, S. Phoenix, P. Deslongchamps, Angew. Chem. 2008, 120, 1292-1295
110. Angew. Chem. Int. Ed. 2008, 47, 1272-1275
111. M. S. Reddy, H. Zhang, S. Phoenix, P. Deslongchamps, Chem. Asian J. 2009, 4, 725-741.
112. For a computational mechanistic study of the Fleming-Tamao oxidation, see:, M. M. Mader, P.-O. Norrby, J. Am. Chem. Soc. 2001, 123, 1970-1976.
113. F. Sondheimer, W. McCrae, W. G. Salmond, J. Am. Chem. Soc. 1969, 91, 1228-1230.
114. G. R. Pettit, D. C. Fessler, K. D. Paull, P. Hofer, J. C. Knight, Can. J. Chem. 1969, 47, 2511-2513
115. G. R. Pettit, J. C. Knight, C. L. Herald, J. Org. Chem. 1970, 35, 1393-1398
116. G. R. Pettit, D. C. Fessler, K. D. Paull, P. Hofer, J. C. Knight, J. Org. Chem. 1970, 35, 1398-1404
117. G. R. Pettit, L. E. Houghton, J. C. Knight, F. Bruschweiler, J. Org. Chem. 1970, 35, 2895-2898
118. G. R. Pettit, J. R. Dias, J. Org. Chem. 1971, 36, 3207-3211.
119. T. Y. R. Tsai, K. Wiesner, Can. J. Chem. 1982, 60, 2161-2163
120. K. Wiesner, T. Y. R. Tsai, F. J. Jaggi, C. S. J. Tsai, G. D. Gray, Helv. Chim. Acta 1982, 65, 2049-2060
121. K. Wiesner, T. Y. R. Tsai, A. Sen, R. Kumar, M. Tsubuki, Helv. Chim. Acta 1983, 66, 2632-2640
122. K. Wiesner, T. Y. R. Tsai, Natural Products Research Center, University of New Brunswick, Fredericton, New Brunswick (Canada), Patent Appl. No. 288,763, 1981. Wiesner's synthethic strategy was also extended to the synthesis of azabufalin, an unnatural bufadienolide derivative containing a C17 β-disposed 2-pyridone in place of the usual 2-pyrone
123. M.-J. Shiao, J. Org. Chem. 1982, 47, 5189-5191.
124. E. Yoshii, T. Oribe, T. Koizumi, I. Hayashi, K. Tumura, Chem. Pharm. Bull. 1977, 25, 2249-2256.
125. M. M. Kabat, A. Kurek, J. Wicha, J. Org. Chem. 1983, 48, 4248-4251.
126. P. E. Bauer, K. S. Kyler, D. S. Watt, J. Org. Chem. 1983, 48, 34-39.
127. It should be noted that palladium-catalyzed cross-couplings employing C17 enol trifluoromethanesulfonates en route to cardenolide products had been described previously:, W. Harnisch, E. Morera, G. Ortar, J. Org. Chem. 1985, 50, 1990-1992.
128. Z. Liu, J. Meinwald, J. Org. Chem. 1996, 61, 6693-6699; for a recent example of a Sonogashira cross-coupling of a steroidal C17 enol trifluoromethanesulfonate with a complex alkyne en route to (+)-cephalostatin 1, see
129. K. C. Fortner, D. Kato, Y. Tanaka, M. D. Shair, J. Am. Chem. Soc. 2010, 132, 275-280.
130. D. C. Behenna, E. J. Corey, J. Am. Chem. Soc. 2008, 130, 6720-6721.
131. G. H. Posner, K. Afarinkia, H. Dai, Org. Synth. 1996, 73, 231-236.
132. E. C. Gravett, P. J. Hilton, K. Jones, F. Romero, Tetrahedron Lett. 2001, 42, 9081-9084.
133. T. Tokuyama, J. W. Daly, B. Witkop, J. Am. Chem. Soc. 1969, 91, 3931-3938.
134. J. P. Dumbacher, A. Wako, S. R. Derrickson, A. Samuelson, T. F. Spande, J. W. Daly, Proc. Natl. Acad. Sci. USA 2004, 101, 15857-15860.
135. S.-Y. Wang, J. Mitchell, D. B. Tikhonov, B. S. Zhorov, G. K. Wang, Mol. Pharmacol. 2006, 69, 1513.
136. H. Heymann, L. F. Fieser, J. Am. Chem. Soc. 1952, 74, 5938-5941.
137. R. R. Schumaker, J. F. W. Keana, J. Chem. Soc. Chem. Commun. 1972, 622
138. J. F. W. Keana, R. R. Schumaker, J. Org. Chem. 1976, 41, 3840-3846.
139. P. Magnus, T. Leapheart, C. Walker, J. Chem. Soc. Chem. Commun. 1985, 1185-1186.
140. W. Graf, H. Berner, F. L. Berner-Fenz, E. Gossinger, R. Imhof, H. Wehrli, Helv. Chim. Acta 1970, 53, 2267-2275
141. R. Imhof, E. Gossinger, W. Graf, W. Schnuriger, H. Wehrli, Helv. Chim. Acta 1971, 54, 2775-2785
142. R. Imhof, E. Gossinger, W. Graf, H. Berner, L. Berner-Fenz, H. Wehrli, Helv. Chim. Acta 1972, 55, 1151-1153
143. W. Graf, E. Gossinger, R. Imhof, H. Wehrli, Helv. Chim. Acta 1972, 55, 1545-1560
144. R. Imhof, E. Gossinger, W. Graf, L. Berner-Fenz, H. Berner, R. Schaufelberger, H. Wehrli, Helv. Chim. Acta 1973, 56, 139-162.
145. C. Meystre, K. Heusler, J. Kalvoda, P. Wieland, G. Anner, A. Wettstein, Helv. Chim. Acta 1962, 45, 1317-1343
146. K. Heusler, P. Wieland, Ch. Meystre, Org. Synth. 1965, 45, 57. For an excellent review of intramolecular free-radical reactions, see
147. K. Heusler, J. Kalvoda, Angew. Chem. 1964, 76, 518-531
148. Angew. Chem. Int. Ed. Engl. 1964, 3, 525-538
149. K. Heusler, J. Kalvoda, Steroids 1996, 61, 492-503.
150. L. F. Fieser, S. Rajagopalan, J. Am. Chem. Soc. 1951, 73, 118.
151. T. J. Grinsteiner, Y. Kishi, Tetrahedron Lett. 1994, 35, 8333-8336
152. T. J. Grinsteiner, Y. Kishi, Tetrahedron Lett. 1994, 35, 8337-8340
153. M. Kurosu, Y. Kishi, J. Org. Chem. 1998, 63, 6100-6101
154. M. Kurosu, L. R. Marcin, T. J. Grinsteiner, Y. Kishi, J. Am. Chem. Soc. 1998, 120, 6627-6628.
155. M. E. Garst, T. A. Spencer, J. Am. Chem. Soc. 1973, 95, 250-252. For Kishi's modification of the Garst-Spencer furan annulation, see
156. M. Kurosu, L. R. Marcin, Y. Kishi, Tetrahedron Lett. 1998, 39, 8929-8932.
157. F. F. Fleming, L. Funk, R. Altundas, Y. Tu, J. Org. Chem. 2001, 66, 6502-6504.
158. V. B. Jigajinni, R. H. Wightman, Tetrahedron Lett. 1982, 23, 117.
159. M. S. Chen, M. C. White, Science 2007, 318, 783-787
160. T. Newhouse, P. S. Baran, Angew. Chem. Int. Ed. 2011, 50, 3362-3374
161. W. R. Gutekunst, P. S. Baran, Chem. Soc. Rev. 2011, 40, 1976-1991, and references therein.
162. A. H. Hoveyda, S. J. Malcolmson, S. J. Meek, A. R. Zhugralin, Angew. Chem. 2010, 122, 38-49
163. Angew. Chem. Int. Ed. 2010, 49, 34-44
164. S. J. Meek, R. V. O'Brien, J. Llaveria, R. R. Schrock, A. H. Hoveyda, Nature 2011, 471, 461-466
165. M. Yu, C. Wang, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Nature 2011, 479, 88-93
166. X. Gao, H. Han, M. J. Krische, J. Am. Chem. Soc. 2011, 133, 12795-12800
167. Y. Lu, S. K. Woo, M. J. Krische, J. Am. Chem. Soc. 2011, 133, 13876-13879, and references therein.
168. C. F. Nising, S. Brase, Angew. Chem. 2008, 120, 9529-9531
169. Angew. Chem. Int. Ed. 2008, 47, 9389-9391
170. C. K. Jana, J. Hoecker, T. M. Woods, H. J. Jessen, M. Neuburger, K. Gademann, Angew. Chem. 2011, 123, 5263-5267
171. Angew. Chem. Int. Ed. 2011, 50, 5157-5161
172. J. Shi, G. Manolikakes, C.-H. Yeh, C. A. Guerrero, R. A. Shenvi, H. Shigehisa, P. S. Baran, J. Am. Chem. Soc. 2011, 133, 8014-8027
173. Y. Shi, L. Jia, Q. Xiao, Q. Lan, X. Tang, D. Wang, M. Li, Y. Ji, T. Zhou, W. Tian, Chem. Asian J. 2011, 6, 786-790
174. W. Li, Y. Dang, J. O. Liu, B. Yu, Chem. Eur. J. 2009, 15, 10356-10359
175. K. Ravindar, M. S. Reddy, L. Lindqvist, J. Pelletier, P. Deslongchamps, J. Org. Chem. 2011, 76, 1269-1284
176. A. Giannis, P. Heretsch, V. Sarli, A. Stobel, Angew. Chem. 2009, 121, 8052-8055
177. Angew. Chem. Int. Ed. 2009, 48, 7911-7914.