Metathesis-Based Synthesis of Complex Bioactives

Modern Tools for the Synthesis of Complex Bioactive Molecules

Volumn , Issue , 2012, Pages 155-188

  Richard, Jean Alexandre ^a   Ng, Sin Yee ^a   Chen, David Y k ^a  

^a Seoul National University   (South Korea)

Author keywords

Metathesis based synthesis of complex bioactives; Ring closing alkyne metathesis; Ring closing olefin metathesis; Tandem metathesis

Indexed keywords

EID: 84884857284     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118342886.ch5     Document Type: Chapter

References (148)

1. Grubbs, R. H. (Ed.), Handbook of Metathesis, Wiley-VCH, Weinheim, 2003.
2. For leading references on the metathesis reaction, H.-G. Schmalz, Angew. Chem. Int. Ed. Engl. 1995, 34, 1833-1836
3. R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452
4. M. Schuster, S. Blechert, Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056
5. R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450
6. A. Fürstner, Angew. Chem., Int. Ed. 2000, 39, 3012-3043
7. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29
8. R. H. Grubbs, Tetrahedron 2004, 60, 7117-7140
9. A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243-251.
10. J.-L. Hérisson, Y. Chauvin, Makromol. Chem. 1970, 141, 161-176
11. C. P. Casey, T. J. Burkhardt, J. Am. Chem. Soc. 1974, 96, 7808-7809
12. T. J. Katz, J. McGinnis, J. Am. Chem. Soc. 1975, 97, 1592-1593
13. R.H.Grubbs,D.D. Carr, C.Hoppin, P. L. Burk, J.Am.Chem. Soc. 1976, 98, 3478-3483.
14. R. R. Schrock, J. S. Murdzek, G. C. Bazan, J. Robins, M. DiMare, M. O'Regan, J. Am. Chem. Soc. 1990, 112, 3875-3886
15. R. R. Schrock, Tetrahedron, 1999, 55, 8141-8153 and references therein
16. For a review on molybdenum and tungsten metathesis catalysts, R. R. Schrock, A. H. Hoveyda, Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
17. P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041
18. P. Schwab, R. H. Grubbs, J. W. Ziller, J. Am. Chem. Soc. 1996, 118, 100-110.
19. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953-956
20. W. A. Herrmann, Angew. Chem., Int. Ed. 2002, 41, 1290-1309
21. T. M. Trnka, J. P. Morgan, M. S. Sanford, T. E. Wilhelm, M. Scholl, T.-L. Choi, S. Ding, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 2546-2558.
22. J. S. Kingsbury, J. P. A. Harrity, P. J. Bonitatebus, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 791-799 and references therein
23. S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168-8179.
24. For a review on this class of metathesis catalysts, A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity, Org. Biomol. Chem. 2004, 2, 8-23.
25. Nobel lectures:Y. Chauvin, Angew. Chem., Int. Ed. 2006, 45, 3740-3765
26. R. R. Schrock, Angew. Chem., Int. Ed. 2006, 45, 3748-3759
27. R. H. Grubbs, Angew. Chem., Int. Ed. 2006, 45, 3760-3765.
28. For insightful reviews on the use of the metathesis reaction in the synthesis of natural products, K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem., Int. Ed. 2006, 44, 4490-4527
29. A. Gradillas, J. Pérez-Castells, Angew. Chem., Int. Ed. 2006, 45, 6086-6101.
30. For reviews on ring-closing olefin metathesis, S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371-388
31. M. E. Maier, Angew. Chem., Int. Ed. 2000, 39, 2073-2077.
32. For recent reviews about this family of natural products, D. Y.-K. Chen, C.-C. Tseng, Org. Biomol. Chem. 2010, 8, 2900-2911
33. A. R. Hardin Narayan, M. Simmons, R. Sarpong, Eur. J. Org. Chem. 2010, 3553-3567.
34. D. T. Craft, B. W. Gung, Tetrahedron. Lett. 2008, 49, 5931-5934.
35. For a reviewon the formation of oxygen- and nitrogen-containing heterocycles byRCM,see A. Deiters, S. F. Martin, Chem. Rev. 2004, 104, 2199-2238.
36. C. J. Douglas, S. Hiebert, L. E. Overman, Org. Lett. 2005, 7, 933-936
37. N. K. Garg, S. Hiebert, L. E. Overman, Angew. Chem., Int. Ed. 2006, 45, 2912-2915
38. M. H. Becker, P. Chua, R. Dowham, C. J. Douglas, N. K. Garg, S. Hiebert, S. Jaroch, R. T. Matsuoka, J. A. Middleton, F. W. Ng, L. E. Overman, J. Am. Chem. Soc. 2007, 129, 11987-12002.
39. R. J. Ferrier, S. Middleton, Chem. Rev. 1993, 93, 2779-2831
40. N. A. Petasis, S. P. Lu, Tetrahedron. Lett. 1996, 37, 141-144
41. A. B. Smith, III, R. J. Fox, T. M. Razler, Acc. Chem. Res. 2008, 41, 675-687.
42. A.B.Smith, III,K.Basu,T. Bosanac, J.Am.Chem. Soc. 2007, 129, 14872-14874
43. A. B.Smith, III, K. Basu, T. Bosanac, J. Am. Chem. Soc. 2009, 131, 2348-2358.
44. For a review on abyssomicins, see K. C. Nicolaou, S. T. Harrison, J. S. Chen, Synthesis 2009, 33-42.
45. K. C. Nicolaou, S. T. Harrison, Angew. Chem., Int. Ed. 2006, 45, 3256-3260
46. K. C. Nicolaou, S. T. Harrison, J. Am. Chem. Soc. 2007, 129, 429-440.
47. For reviews on PPAPs, see R. Ciochina, R. B. Grossman, Chem. Rev. 2006, 106, 3963
48. I. P. Singh, J. Sidana, S. B. Bharate, W. J. Foley, Nat. Prod. Rep. 2010, 27, 393-416.
49. A. Kuramochi, H. Usuda, K. Yamatsugu, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 14200-14201.
50. X. Jiang, B. Liu, S. Lebreton, J. K. De Brabander, J. Am. Chem. Soc. 2007, 129, 6386-6387
51. K. C. Nicolaou, R. Guduru, Y.-P. Sun, B. Banerji,D. Y.-K. Chen, Angew. Chem., Int. Ed. 2007, 46, 5896-5900.
52. K. C. Nicolaou, Y.-P. Sun, R. Guduru, B. Banerji, D. Y.-K. Chen, J. Am. Chem. Soc. 2008, 130, 3633-3644.
53. For a recent review on kendomycin, see H. J. Martin, T. Magauer, J. Mulzer, Angew. Chem., Int. Ed. 2010, 49, 5614-5626.
54. J. Mulzer, S. Pichlmair, M. P. Green, M. M. B. Marques, H. J. Martin, Proc. Natl. Acad. Sci. USA 2004, 101, 11980-11985.
55. T. Magauer, H. J. Martin, J. Mulzer, Angew. Chem., Int. Ed. 2009, 48, 6032-6036
56. T. Magauer, H. J. Martin, J. Mulzer, Chem. Eur. J. 2010, 16, 507-519.
57. I. S. Young, J. L.Williams, M. A. Kerr, Org. Lett, 2005, 7, 953-955
58. I. S. Young, M. A. Kerr, J. Am. Chem. Soc. 2007, 129, 1465-1469.
59. T. Nagata, M. Nakagawa, A. Nishida, J. Am. Chem. Soc. 2003, 125, 7484-7485
60. K. Ono, M. Nakagawa, A. Nishida, Angew. Chem., Int. Ed. 2004, 43, 2020-2023.
61. P. Jakubec, D. M. Cockfield, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 16632-16633.
62. P. Compain, Adv. Synth. Catal. 2007, 349, 1829-1846.
63. A. Fürstner, G. Seidel, Angew. Chem., Int. Ed. 1998, 37, 1734-1736
64. A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108-11113
65. A. Fürstner, P. W. Davies, Chem. Commun. 2005, 2307-2320.
66. A. Fürstner, G. Seidel, J. Organomet. Chem. 2000, 606, 75-78.
67. V.V. Vintonyak, M. E. Maier, Org. Lett. 2007, 9, 655-658
68. V.V. Vintonyak, M. E. Maier, Angew. Chem., Int. Ed. 2007, 46, 5209-5211
69. V. V. Vintonyak, M. Calá, F. Lay, B. Kunze, F. Sasse, M. E. Maier, Chem. Eur. J. 2008, 14, 3709-3720.
70. For a similar strategy from Fürstner et al., A. Fürstner, M. Bindl, L. Jean, Angew. Chem., Int. Ed. 2007, 46, 9275-9278
71. M. Bindl, L. Jean, J. Herrmann, R. Müller, A. Fürstner, Chem. Eur. J. 2009, 15, 12310-12319.
72. A. Fürstner,O. Larionov, S. Flügge, Angew. Chem., Int. Ed. 2007, 46, 5545-5548
73. A. Fürstner, S. Flügge, O. Larionov, Y. Takahashi, T. Kubota, J. Kobayashi, Chem. Eur. J. 2009, 15, 4011-4029.
74. For a reviewon olefin cross-metathesis, see S. J. Connon, S. Blechert, Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
75. M.T. Crimmins, H. S. Christie, K. Chaudhary, A. Long, J. Am. Chem. Soc. 2005, 127, 13810-13812
76. M. T. Crimmins, H. S. Christie, A. Long, K. Chaudhary, Org. Lett. 2009, 11, 831-834.
77. B. J. Albert, A. Sivaramakrishnan, T. Naka, K. Koide, J. Am. Chem. Soc. 2006, 128, 2792-2793
78. B. J. Albert, A. Sivaramakrishnan, T. Naka, N. L. Czaicki, K. Koide, J. Am. Chem. Soc. 2007, 129, 2648-2659.
79. F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504-540
80. A. Bermejo, B. Figadère, M.-C. Zafra-Polo, I. Barrachina, E. Estornell, D. Cortes, Nat. Prod. Rep. 2005, 22, 269-303.
81. T. J. Donohoe, R. M. Harris, J. Burrows, J. Parker, J. Am. Chem. Soc. 2006, 128, 13704-13705
82. T. J. Donohoe, R. M. Harris, O.Williams, G. C. Hargaden, J. Burrows, J. Parker, J. Am. Chem. Soc. 2009, 131, 12854-12861.
83. For a review on the application of olefin metathesis in chemical biology, J. B. Binder, R. T. Raines, Curr. Opin. Chem. Biol. 2008, 12, 767-773.
84. J. Zhu, Q. Wan, G. Ragupathi, C. M. George, P. O. Livingston, S. J. Danishefsky, J. Am. Chem. Soc. 2009, 131, 4151-4158.
85. Y. A. Lin, J. M. Chalker, N. Floyd, G. J. L. Bernardes, B. G. Davis, J. Am. Chem. Soc. 2008, 130, 9642-9643.
86. For reviews on enyne metathesis, see S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382
87. S.V. Maifeld, D. Lee, Chem. Eur. J. 2005, 11, 6118-6126
88. E. C. Hansen, D. Lee, Acc. Chem. Res. 2006, 39, 509-519.
89. C. Baumgartner, S. Ma, Q. Liu, B. Stoltz, Org. Biomol. Chem. 2010, 8, 2915-2917.
90. H. M.Ko, C.W. Lee, H. K. Kwon, H. S. Chung, S.Y. Choi,Y. K. Chung, E. Lee, Angew. Chem., Int. Ed. 2009, 48, 2364-2366.
91. M. Movassaghi, G. Piizzi, D. S. Siegel, G. Piersanti, Angew. Chem., Int. Ed. 2006, 45, 5859-5863
92. D. S. Siegel, G. Piizzi, G. Piersanti, M. Movassaghi, J. Org. Chem. 2009, 74, 9292-9304.
93. S. Mukherjee, D. Lee., Org. Lett. 2009, 11, 2916-2919.
94. T. A. Dineen, W. R. Roush, Org. Lett. 2004, 6, 2043-2046.
95. A. Le Flohic, C. Meyer, J. Cossy, Org. Lett. 2005, 7, 339-342.
96. K. A. Tony, D. Dabideen, J. Li, M. D. Diaz-Hernández, J. Jiménez-Barbero, D. R. Mootoo, J. Org. Chem. 2009, 74, 7774-7780.
97. P. K. M. Venukadasula, R. Chegondi, S. Maitra, P. R. Hanson, Org. Lett. 2010, 12, 1556-1559.
98. For a short review of this concept, see D. J. Wallace, Angew. Chem., Int. Ed. 2005, 44, 1912-1915.
99. E. C. Hansen, D. Lee, Org. Lett. 2004, 6, 2035-2038
100. T. R. Hoye, C. S. Jeffrey, M.A. Tennakoon, J. Wang, H. Zhao, J. Am. Chem. Soc. 2004, 126, 10210-10211. and references therein.
101. X.Wang, E. J. Bowman, B. J. Bowman, J. A. Porco, Jr., Angew. Chem., Int. Ed. 2004, 43, 3601-3605.
102. P. A. Roethle, I. T. Chen, D. Trauner, J. Am. Chem. Soc. 2007, 129, 8960-8961.
103. E. J. Cho, D. Lee, Org. Lett. 2008, 10, 257-259.
104. C. C. Marvin, E. A. Voight, S. D. Burke, Org. Lett. 2007, 9, 5357-5359
105. C. C. Marvin, E. A. Voight, J. M. Suh, C. L. Paradise, S. D. Burke, J. Org. Chem. 2008, 73, 8452-8457.
106. For reviews on cascade reactions in organic synthesis, see L. F. Tietze, U. Beifuss, Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163
107. L. F. Tietze, Chem. Rev. 1996, 96, 115-136
108. L. F. Tietze, G. Brasche, K. Gericke, Domino Reactions in Organic Synthesis,Wiley-VCH,Weinheim, 2006
109. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem., Int. Ed. 2006, 45, 7134-7186
110. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993-3009.
111. For reviews on olefin metathesis-based cascade reactions, see O. Arjona, A. G. Csákÿ, J. Plumet, Eur. J. Org. Chem. 2003, 611-622
112. N. Holub, S. Blechert, Chem. Asian J. 2007, 2, 1064-1082.
113. J. R. Stille, R. H. Grubbs, J. Am. Chem. Soc. 1986, 108, 855-856.
114. F. N. Tebbe, G.W. Parshall, G. S. Reddy, J. Am. Chem. Soc. 1978, 100, 3611-3613
115. K. C. Rana, Synlett, 2007, 1795-1796.
116. Selected examples: C. L. Chandler,A. J. Phillips, Org. Lett. 2005, 7, 3493-3495
117. A. C. Hart, A. J. Phillips, J. Am. Chem. Soc. 2006, 128, 1094-1095
118. J. A. Henderson, A. J. Phillips, Angew. Chem., Int. Ed. 2008, 47, 8499-8501
119. K. L. Jackson, J. A. Henderson, H. Motoyoshi, A. J. Phillips, Angew. Chem., Int. Ed. 2009, 48, 2346-2350.
120. M. W. B. Pfeiffer, A. J. Phillips, J. Am. Chem. Soc. 2005, 127, 5334-5335.
121. D. A. Kummer, J. B. Brenneman, S. F. Martin, Org. Lett. 2005, 7, 4621-4623.
122. H. Fukumoto, K. Takahashi, J. Ishihara, S. Hatakeyama, Angew. Chem., Int. Ed. 2006, 45, 2731-2734.
123. T. R. Hoye, B. M. Eklov, J. Jeon, M. Khoroosi, Org. Lett. 2006, 8, 3383-3386.
124. T. Shimizu, T. Satoh, K. Murakoshi, M. Sodeoka, Org. Lett. 2005, 7, 5573-5576.
125. J. Marjanovic, S. A. Kozmin, Angew. Chem., Int. Ed. 2007, 46, 8854-8857.
126. For reviews on enantioselective desymmetrizations, see E. Schoffers, A. Golebiowski, C. R. Johnson, Tetrahedron, 1996, 52, 3769-3826
127. M. C. Willis, J. Chem. Soc., Perkin Trans. 1, 1999, 1765-1784
128. A.C. Spivey, B. I.Andrews, Angew.Chem., Int.Ed. 2001, 41, 3131-3134;
129. M. Anstiss, J. M. Holland, A. Nelson, J. R. Titchmarsh, Synlett, 2003, 1213-1220
130. M. Lautens, K. Fagnou, S. Hiebert, Acc. Chem. Res. 2003, 36, 48-58
131. R. W. Hoffmann, Angew. Chem., Int. Ed. 2003, 42, 1096-1109
132. K. Mikami, M. Yamanaka, Chem.Rev. 2003, 103, 3369-3400
133. Y. Chen, P.McDaid, L. Deng, Chem. Rev. 2003, 103, 2965-2983
134. S.-K. Tian,Y. Chen, J.Hang, L. Tang, P.McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621-631
135. E. Garcia-Urdiales, I. Alfonso, V. Gotor, Chem. Rev. 2005, 105, 313-354
136. I. Atodiresei, I. Schiffers, C. Bolm, Chem. Rev. 2007, 107, 5683-5712.
137. S. D. Burke, N. Müller, C. M. Beaudry, Org. Lett. 1999, 1, 1827-1829.
138. For a review on catalytic asymmetric olefin metathesis, see A. H. Hoveyda, R. R. Schrock, Chem. Eur. J. 2001, 7, 945-950.
139. For reviews on catalytic enantioselective olefin metathesis in natural product synthesis, see R. R. Schrock, A. H. Hoveyda, Angew. Chem., Int. Ed. 2003, 42, 4592-4633
140. A. H. Hoveyda, S. J. Malcolmson, S. J. Meek, A. R. Zhugralin, Angew. Chem., Int. Ed. 2010, 49, 34-44.
141. G. S.Weatherhead, G. A. Cortez, R. R. Schrock, A. H. Hoveyda, Proc. Natl. Acad. Sci. USA 2004, 101, 5805-5809.
142. D. G. Gillingham, A. H. Hoveyda, Angew. Chem., Int. Ed. 2007, 46, 3860-3864.
143. S. J. Malcolmson, S. J. Meek, E. S. Sattely, R. R. Schrock, A. H. Hoveyda, Nature 2008, 456, 933-937
144. E. S. Sattely, S. J. Meek, S. J. Malcolmson, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 943-953
145. S. J. Meek, S. J. Malcolmson, B. Li, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 16407-16409.
146. K. C. Nicolaou, G.Vassilikogiannakis,T. Montagnon, Angew. Chem., Int. Ed. 2002, 41, 3276-3281
147. K. C. Nicolaou, T. Montagnon, G. Vassilikogiannakis, C. J. N. Mathison, J. Am. Chem. Soc. 2005, 127, 8872-8888.
148. M. E. Layton, C. A. Morales, M. D. Shair, J. Am. Chem. Soc. 2002, 124, 773-774.