Atom-Economical Dimerization Strategy by the Rhodium-Catalyzed Addition of Carboxylic Acids to Allenes: Protecting-Group-Free Synthesis of Clavosolide A and Late-Stage Modification

Angewandte Chemie - International Edition

Volumn 54, Issue 51, 2015, Pages 15530-15534

  Haydl, Alexander M ^a   Breit, Bernhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

allenes; allylic compounds; natural products; rhodium; total synthesis

Indexed keywords

BIOACTIVITY; C (PROGRAMMING LANGUAGE); CARBOXYLIC ACIDS; CATALYSIS; DIMERIZATION; HYDROCARBONS; KETONES; RHODIUM; SYNTHESIS (CHEMICAL);

ALLENES; ALLYLIC COMPOUNDS; CONVERGENT SYNTHESIS; NATURAL PRODUCTS; PROTECTING-GROUP-FREE SYNTHESIS; RHODIUM-CATALYZED; STRUCTURAL MOTIFS; TOTAL SYNTHESIS;

RHODIUM COMPOUNDS;

ALKADIENE; CARBOXYLIC ACID; CLAVOSOLIDE A; MACROLIDE; PROPADIENE; RHODIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; SYNTHESIS;

ALKADIENES; CARBOXYLIC ACIDS; CATALYSIS; DIMERIZATION; MACROLIDES; MOLECULAR STRUCTURE; RHODIUM;

EID: 84955208049     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201506618     Document Type: Article

References (125)

1. G. Lian, B. Yu, Chem. Biodiversity 2010, 7, 2660-2691.
2. E. J. Kang, E. Lee, Chem. Rev. 2005, 105, 4348-4378.
3. E. M. Driggers, S. P. Hale, J. Lee, N. K. Terrett, Nat. Rev. Drug Discovery 2008, 7, 608-624;
4. E. Marsault, M. L. Peterson, J. Med. Chem. 2011, 54, 1961-2004;
5. B. Proska, Ceska Slov. Farm. 2000, 49, 221-228.
6. E. J. Corey, K. C. Nicolaou, T. Toru, J. Am. Chem. Soc. 1975, 97, 2287-2288;
7. K. F. Burri, R. A. Cardone, W. Y. Chen, P. Rosen, J. Am. Chem. Soc. 1978, 100, 7069-7071;
8. A. Zajícová, M. Múcková, M. Krulová, Z. Rychnavská, V. Holán, Int. Immunopharmacol. 2001, 1, 1939-1945;
9. R. Barth, J. Mulzer, Angew. Chem. Int. Ed. 2007, 46, 5791-5794;
10. Angew. Chem. 2007, 119, 5893-5896;
11. K. C. Nicolaou, A. L. Nold, R. R. Milburn, C. S. Schindler, K. P. Cole, J. Yamaguchi, J. Am. Chem. Soc. 2007, 129, 1760-1768;
12. P. A. Evans, M.-H. Huang, M. J. Lawler, S. Maroto, Nat. Chem. 2012, 4, 680-684;
13. H. C. Kwon, C. A. Kauffman, P. R. Jensen, W. Fenical, J. Am. Chem. Soc. 2006, 128, 1622-1632;
14. A. Fürstner, M. Albert, J. Mlynarski, M. Matheu, E. DeClerq, J. Am. Chem. Soc. 2003, 125, 13132-13142;
15. E. J. Kang, E. J. Cho, Y. E. Lee, M. K. Ji, D. M. Shin, Y. K. Chung, E. Lee, J. Am. Chem. Soc. 2004, 126, 2680-2681;
16. I. Paterson, J. D. Smith, R. A. Ward, J. G. Cumming, J. Am. Chem. Soc. 1994, 116, 2615-2616.
17. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993;
18. H. Tone, T. Nishi, Y. Oikawa, M. Hikota, O. Yonemitsu, Tetrahedron Lett. 1987, 28, 4569;
19. M. Hikota, H. Tone, K. Horita, O. Yonemitsu, Tetrahedron 1990, 46, 4613;
20. M. Hikota, Y. Sakurai, K. Horita, O. Yonemitsu, Tetrahedron Lett. 1990, 31, 6367.
21. B. M. Trost, A. Quintard, Angew. Chem. Int. Ed. 2012, 51, 6704-6708;
22. Angew. Chem. 2012, 124, 6808-6812;
23. T. Nishimaru, M. Kondo, K. Takeshita, K. Takahashi, J. Ishihara, S. Hatakeyama, Angew. Chem. Int. Ed. 2014, 53, 8459-8462;
24. Angew. Chem. 2014, 126, 8599-8602;
25. M. R. Gesinski, S. D. Rychnovski, J. Am. Chem. Soc. 2011, 133, 9727-9729;
26. A. W. H. Speed, T. J. Mann, R. V. O'Brien, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2014, 136, 16136-16139;
27. K. J. Ralston, H. C. Ramstadius, R. C. Brewster, H. S. Niblock, A. N. Hulme, Angew. Chem. Int. Ed. 2015, 54, 7086-7090;
28. Angew. Chem. 2015, 127, 7192-7196.
29. M. L. Cooke, K. Xu, B. Breit, Angew. Chem. Int. Ed. 2012, 51, 10876-10879;
30. Angew. Chem. 2012, 124, 11034-11037;
31. K. Xu, N. Thieme, B. Breit, Angew. Chem. Int. Ed. 2014, 53, 2162-2165;
32. Angew. Chem. 2014, 126, 2194-2197;
33. K. Xu, N. Thieme, B. Breit, Angew. Chem. Int. Ed. 2014, 53, 7268-7271;
34. Angew. Chem. 2014, 126, 7396-7399;
35. C. Li, B. Breit, J. Am. Chem. Soc. 2014, 136, 862-865;
36. C. Li, M. Kähny, B. Breit, Angew. Chem. Int. Ed. 2014, 53, 13780-13784;
37. Angew. Chem. 2014, 126, 14000-14004;
38. A. B. Pritzius, B. Breit, Angew. Chem. Int. Ed. 2015, 54, 3121-3125;
39. Angew. Chem. 2015, 127, 3164-3168;
40. A. M. Haydl, K. Xu, B. Breit, Angew. Chem. Int. Ed. 2015, 54, 7149-7153;
41. Angew. Chem. 2015, 127, 7255-7259.
42. R. Zimmer, C. Dinesh, E. Nandanan, A. F. Khan, Chem. Rev. 2000, 100, 3067-3125;
43. I. S. Kim, M. J. Krische, Org. Lett. 2008, 10, 513-515;
44. T. Kawamoto, S. Hirabayashi, X. Guo, T. Nishimura, T. Hayashi, Chem. Commun. 2009, 3528-3530;
45. J. Moran, A. Preetz, R. A. Mesch, M. J. Krische, Nat. Chem. 2011, 3, 287-290;
46. B. M. Trost, W. Brieden, Angew. Chem. Int. Ed. Engl. 1992, 31, 1335-1336;
47. Angew. Chem. 1992, 104, 1392-1394;
48. L. M. Lutete, I. Kadota, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 1622-1623.
49. P. Koschker, A. Lumbroso, B. Breit, J. Am. Chem. Soc. 2011, 133, 20746-20749;
50. C. Schotes, D. Ostrovskyi, J. Senger, K. Schmidtkunz, M. Jung, B. Breit, Chem. Eur. J. 2014, 20, 2164-2168.
51. A. Lumbroso, P. Koschker, N. R. Vautravers, B. Breit, J. Am. Chem. Soc. 2011, 133, 2386-2389;
52. A. Lumbroso, N. Abermil, B. Breit, Chem. Sci. 2012, 3, 789-793.
53. B. M. Trost, Chem. Rev. 1996, 96, 395-422;
54. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943;
55. Z. Lu, S. Ma, Angew. Chem. Int. Ed. 2008, 47, 258-297;
56. Angew. Chem. 2008, 120, 264-303;
57. D. C. Vrieze, G. S. Hoge, P. Z. Hoerter, J. T. Van Haitsma, B. M. Samas, Org. Lett. 2009, 11, 3140-3142;
58. T. Hayashi, A. Okada, T. Suzuka, M. Kawatsura, Org. Lett. 2003, 5, 1713-1715;
59. P. A. Evans, D. K. Leahy, J. Am. Chem. Soc. 2002, 124, 7882-7883.
60. G. Liu, Y. Wu, Top. Curr. Chem. 2010, 292, 195-209;
61. M. S. Chen, M. C. White, J. Am. Chem. Soc. 2004, 126, 1346-1347;
62. G. Liu, S. S. Stahl, J. Am. Chem. Soc. 2007, 129, 6328-6335;
63. G. Yin, Y. Wu, G. Liu, J. Am. Chem. Soc. 2010, 132, 11978-11987.
64. A. Lumbroso, M. L. Cooke, B. Breit, Angew. Chem. Int. Ed. 2013, 52, 1890-1932;
65. Angew. Chem. 2013, 125, 1942-1986.
66. R. M. Rao, D. J. Faulkner, J. Nat. Prod. 2002, 65, 386-388;
67. K. L. Erickson, K. R. Gustafson, L. K. Pannell, J. A. Beutler, M. R. Boyd, J. Nat. Prod. 2002, 65, 1303-1306.
68. A. R. Pereira, C. F. McCue, W. H. Gerwick, J. Nat. Prod. 2010, 73, 217-220.
69. For prior syntheses of the clavosolide family, see:
70. C. S. Barry, J. D. Elsworth, P. T. Seden, N. Bushby, J. R. Harding, R. W. Alder, C. L. Willis, Org. Lett. 2006, 8, 3319-3322;
71. P. T. Seden, J. P. H. Charmant, C. L. Willis, Org. Lett. 2008, 10, 1637-1640;
72. J. B. Son, S. N. Kim, N. Y. Kim, D. H. Lee, Org. Lett. 2006, 8, 661-664;
73. V. Simov, A. B. Smith III, Org. Lett. 2006, 8, 3315-3318;
74. T. K. Chakraborty, V. R. Reddy, P. K. Gajula, Tetrahedron 2008, 64, 5162-5167;
75. J. D. Carrick, M. P. Jennings, Org. Lett. 2009, 11, 769-772;
76. G. Peh, P. E. Floreancig, Org. Lett. 2012, 14, 5614-5617.
77. For prior syntheses of cyanolide A, see:
78. H. Kim, J. Hong, Org. Lett. 2010, 12, 2880-2883;
79. A. K. Hajare, V. Ravikumar, S. Khaleel, D. Bhuniya, D. S. Reddy, J. Org. Chem. 2011, 76, 963-966;
80. Z. Yang, X. Xie, P. Jing, G. Zhao, J. Zheng, C. Zhao, X. She, Org. Biomol. Chem. 2011, 9, 984-986;
81. S. Pabbaraja, K. Satyanarayana, B. Ganganna, J. S. Yadav, J. Org. Chem. 2011, 76, 1922-1925;
82. G. C. Tay, M. R. Gesinski, S. D. Rychnovsky, Org. Lett. 2013, 15, 4536-4539;
83. R. J. Sharpe, M. P. Jennings, J. Org. Chem. 2011, 76, 8027-8032;
84. A. R. Waldeck, M. J. Krische, Angew. Chem. Int. Ed. 2013, 52, 4470-4473;
85. Angew. Chem. 2013, 125, 4566-4569; and Ref. [6c].
86. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4490-4527;
87. Angew. Chem. 2005, 117, 4564-4601;
88. A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
89. Angew. Chem. 2000, 112, 3140-3172;
90. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29.
91. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050;
92. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861-2904.
93. C. S. Barry, N. Bushby, J. R. Harding, C. L. Willis, Org. Lett. 2005, 7, 2683-2686.
94. R. M. Wilson, S. J. Danishefsky, Angew. Chem. Int. Ed. 2010, 49, 6032-6056;
95. Angew. Chem. 2010, 122, 6168-6193;
96. A. M. Szpilman, E. M. Carreira, Angew. Chem. Int. Ed. 2010, 49, 9592-9628;
97. Angew. Chem. 2010, 122, 9786-9823;
98. A. Fürstner, Isr. J. Chem. 2011, 51, 329-345;
99. J.-Y. Wach, K. Gademann, Synlett 2012, 163-170.
100. J. Nokami, K. Nomiyama, S. Matsuda, N. Imai, K. Kataoka, Angew. Chem. Int. Ed. 2003, 42, 1273-1276;
101. Angew. Chem. 2003, 115, 1311-1314.
102. W. G. Dauben, V. P. Rocco, G. Shapiro, J. Org. Chem. 1985, 50, 3155-3160.
103. For further details, see the Supporting Information.
104. The modified Nokami crotyl-transfer reagent 6 b is a new reagent and was prepared in three steps from commercially available (R)-pulegone. For further details, see the Supporting Information.
105. R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed. Engl.Angew. Chem. Int. Ed. 1980, 19, 731-732;
106. Angew. Chem. 1980, 92, 763-764;
107. R. R. Schmidt, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
108. R. Lopez, A. Fernandez-Mayoralas, J. Org. Chem. 1994, 59, 737-745, and Ref. [17g].
109. H. Lönn, J. Carbohydr. Chem. 1987, 6, 301-306, and Ref. [17g].
110. For further details concerning the transformation of 12 and 14 into 3 to confirm their relative configuration, see the Supporting Information.
111. 1 homologation through cross-metathesis with propene or (Z)-butene analogues, see:
112. S. Imhof, S. Randl, S. Blechert, Chem. Commun. 2001, 1692-1693;
113. C. J. Morten, T. F. Jamison, J. Am. Chem. Soc. 2009, 131, 6678-6679.
114. Cross-metathesis with higher olefins is more common and usually gives better E/Z product ratios; see:
115. T. Seiser, F. Kamena, N. Cramer, Angew. Chem. Int. Ed. 2008, 47, 6483-6485;
116. Angew. Chem. 2008, 120, 6583-6585;
117. S. A. Snyder, A. P. Brucks, D. S. Treitler, I. Moga, J. Am. Chem. Soc. 2012, 134, 17714-17721; and Ref. [9b].
118. B. M. Trost, J. L. Gunzer, O. Dirat, Y. H. Rhee, J. Am. Chem. Soc. 2002, 124, 10396-10415;
119. D. P. Curran, T. Furukawa, Org. Lett. 2002, 4, 2233-2235.
120. The diastereoselectivity of this reaction could not be determined easily, but is known to be high in transformations with related structures; see Refs. [16a,b].
121. B. Breit, Angew. Chem. Int. Ed. 2005, 44, 6816-6825;
122. Angew. Chem. 2005, 117, 6976-6986;
123. B. Breit, W. Seiche, J. Am. Chem. Soc. 2003, 125, 6608-6609.
124. J. U. Rhee, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 10674-10675.
125. P. Wipf, S. R. Spencer, J. Am. Chem. Soc. 2005, 127, 225-235.