Cyclohexyne cycloinsertion in the divergent synthesis of guanacastepenes

Chemistry - A European Journal

Volumn 18, Issue 49, 2012, Pages 15761-15771

  Gampe, Christian M ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

cyclohexyne; cycloinsertion; guanacastepene; natural products; total synthesis

Indexed keywords

CYCLOHEXYNE; CYCLOINSERTION; GUANACASTEPENE; NATURAL PRODUCTS; TOTAL SYNTHESIS;

REACTION INTERMEDIATES; SCAFFOLDS;

CARBON;

CYCLOBUTANE DERIVATIVE; CYCLOBUTANOL; CYCLOHEXANE DERIVATIVE; DITERPENE; GUANACASTEPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CYCLOBUTANES; CYCLOHEXANES; DITERPENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84870032012     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202222     Document Type: Article

References (147)

1. C. A. Arias, B. E. Murray, New Engl. J. Med. 2009, 360, 439-443
2. M. L. Cohen, Nature 2000, 406, 762-767.
3. D. J. Newman, G. M. Cragg, K. M. Snader, J. Nat. Prod. 2003, 66, 1022-1037
4. M. S. Butler, J. Nat. Prod. 2004, 67, 2141-2153
5. D. J. Newman, G. M. Cragg, J. Nat. Prod. 2007, 70, 461-477.
6. D. L. Hawksworth, Mycol. Res. 1991, 95, 641-655
7. H. Yu, L. Zhang, L. Li, C. Zheng, L. Guo, W. Li, P. Sun, L. Qin, Microbiol. Res. 2010, 165, 437-449.
8. S. F. Brady, M. P. Singh, J. E. Janso, J. Clardy, J. Am. Chem. Soc. 2000, 122, 2116-2117
9. S. F. Brady, S. M. Bondi, J. Clardy, J. Am. Chem. Soc. 2001, 123, 9900-9901
10. M. P. Singh, J. E. Janso, S. W. Luckman, S. F. Brady, J. Clardy, M. Greenstein, W. M. Maiese, J. Antibiot. 2000, 53, 256-261.
11. B. Sampson, R. Misra, S. Benson, Genetics 1989, 122, 491-501.
12. B. B. Snider, N. A. Hawryluk, Org. Lett. 2001, 3, 569-572
13. P. Magnus, M. J. Waring, C. Ollivier, V. Lynch, Tetrahedron Lett. 2001, 42, 4947-4950, erratum
14. P. Magnus, M. J. Waring, C. Ollivier, V. Lynch, Tetrahedron Lett. 2001, 42, 6977
15. G. B. Dudley, S. J. Danishefsky, Org. Lett. 2001, 3, 2399-2402
16. G. B. Dudley, D. S. Tan, G. Kim, J. M. Tanski, S. J. Danishefsky, Tetrahedron Lett. 2001, 42, 6789-6791
17. B. B. Snider, B. Shi, Tetrahedron Lett. 2001, 42, 9123-9126
18. G. Mehta, J. D. Umarye, Org. Lett. 2002, 4, 1063-1066
19. S. N. Gradl, J. J. Kennedy-Smith, J. Kim, D. Trauner, Synlett 2002, 411-414
20. T. M. Nguyen, D. Lee, Tetrahedron Lett. 2002, 43, 4033-4036
21. G. Mehta, J. D. Umarye, V. Gagliardini, Tetrahedron Lett. 2002, 43, 6975-6978
22. A. Nakazaki, U. Sharma, M. A. Tius, Org. Lett. 2002, 4, 3363-3366
23. F. D. Boyer, I. Hanna, Tetrahedron Lett. 2002, 43, 7469-7472
24. P. Magnus, C. Ollivier, Tetrahedron Lett. 2002, 43, 9605-9609
25. W. D. Shipe, E. J. Sorensen, Org. Lett. 2002, 4, 2063-2066
26. T. M. Nguyen, R. J. Seifert, D. R. Mowrey, D. Lee, Org. Lett. 2002, 4, 3959-3962
27. G. Mehta, J. D. Umarye, K. Srinivas, Tetrahedron Lett. 2003, 44, 4233-4237
28. X. Du, H. V. Chu, O. Kwon, Org. Lett. 2003, 5, 1923-1926
29. K. M. Brummond, D. Gao, Org. Lett. 2003, 5, 3491-3494
30. C. C. Hughes, J. J. Kennedy-Smith, D. Trauner, Org. Lett. 2003, 5, 4113-4115
31. R. Sarpong, J. T. Su, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 13624-13625
32. S. Srikrishna, D. H. Dethe, Org. Lett. 2004, 6, 165-168
33. P. Chiu, S. Li, Org. Lett. 2004, 6, 613-616
34. X. Du, H. V. Chu, O. Kwon, Tetrahedron Lett. 2004, 45, 8843-8846
35. C. C. Hughes, A. K. Miller, D. Trauner, Org. Lett. 2005, 7, 3425-3428
36. C.-C. Li, X.-H. Zhang, Z.-X. Xie, J.-H. Chen, Z. Yang, Org. Lett. 2005, 7, 3709-3712
37. C.-C. Li, C.-H. Wang, B. Liang, X.-H. Zhang, L.-J. Deng, S. Liang, J.-H. Chen, Y.-D. Wu, Z. Yang, J. Org. Chem. 2006, 71, 6892-6897
38. C. A. McGowan, A.-K. Schmieder, L. Roberts, M. F. Greaney, Org. Biomol. Chem. 2007, 5, 1522-1524
39. K. Michalak, M. Michalak, J. Wicha, Tetrahedron Lett. 2008, 49, 6807-6809; for formal synthesis of guanacastepene A, see
40. B. Shi, N. A. Hawryluk, B. B. Snider, J. Org. Chem. 2003, 68, 1030-1042
41. F.-D. Boyer, I. Hanna, L. Ricard, Org. Lett. 2004, 6, 1817-1820
42. K. Michalak, M. Michalak, J. Wicha, Tetrahedron Lett. 2010, 51, 4344-4346; for a review of the synthetic studies, see
43. M. Hiersemann, H. Helmboldt, Top. Curr. Chem. 2005, 243, 73-136
44. S. V. Maifeld, D. Lee, Synlett 2006, 1623-1644.
45. D. S. Tan, G. B. Dudley, S. Danishefsky, Angew. Chem. 2002, 114, 2289-2292
46. Angew. Chem. Int. Ed. 2002, 41, 2185-2188
47. S. N. Lin, G. B. Dudley, D. S. Tan, S. J. Danishefsky, Angew. Chem. 2002, 114, 2292-2295
48. Angew. Chem. Int. Ed. 2002, 41, 2188-2191; guanacastepene C
49. G. Mehta, K. Palavi, J. D. Umarye, Chem. Commun. 2005, 4456-4458; guanacastepene E
50. W. D. Shipe, E. J. Sorensen, J. Am. Chem. Soc. 2006, 128, 7025-7035
51. A. K. Miller, C. C. Hughes, J. J. Kennedy-Smith, S. N. Gradl, D. Trauner, J. Am. Chem. Soc. 2006, 128, 17057-17062; guanacastepene N
52. S. Iimura, L. E. Overman, R. Paulini, A. Zakarian, J. Am. Chem. Soc. 2006, 128, 13095-13101.
53. C. M. Gampe, S. Boulos, E. M. Carreira, Angew. Chem. 2010, 122, 4186-4189
54. Angew. Chem. Int. Ed. 2010, 49, 4092-4095
55. C. M. Gampe, E. M. Carreira, Angew. Chem. 2011, 123, 3019-3022
56. Angew. Chem. Int. Ed. 2011, 50, 2962-2965
57. for a recent review of the use of arynes and cyclohexyne in natural product synthesis, see:, C. M. Gampe, E. M. Carreira, Angew. Chem. 2012, 124, 3829-3842
58. Angew. Chem. Int. Ed. 2012, 51, 3766-3778.
59. Y. Horiguchi, S. Matsuzawa, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1986, 27, 4025-4028
60. S. Matsuzawa, Y. Horiguchi, E. Nakamura, I. Kuwajima, Tetrahedron 1989, 45, 349-362
61. H. Sakata, Y. Aoki, I. Kuwajima, Tetrahedron Lett. 1990, 31, 1161-1164.
62. T. Mukhopadhyay, D. Seebach, Helv. Chim. Acta 1982, 65, 385-391.
63. For a review on the Friedel-Crafts acylation of alkenes, see:, J. K. Groves, Chem. Soc. Rev. 1972, 1, 73-97.
64. B. M. Trost, T. A. Grese, D. M. T. Chan, J. Am. Chem. Soc. 1991, 113, 7350-7362.
65. B. H. Lipshutz, M. Koerner, D. A. Parker, Tetrahedron Lett. 1987, 28, 945-948.
66. R. T. Hansen, D. B. Carr, J. Schwartz, J. Am. Chem. Soc. 1978, 100, 2244-2245
67. J. Schwartz, D. B. Carr, R. T. Hansen, F. M. Dayrit, J. Org. Chem. 1980, 45, 3053-3061.
68. S. Kim, J. H. Park, Synlett 1995, 163-164.
69. M. Eriksson, T. Iliefski, M. Nilsson, T. Olsson, J. Org. Chem. 1997, 62, 182-187.
70. W. F. Bailey, J. D. Brubaker, K. P. Jordan, J. Organomet. Chem. 2003, 681, 210-214.
71. T. Veysoglu, L. A. Mitscher, J. K. Swayze, Synthesis 1980, 807-810.
72. Y.-L. Zhong, T. K. M. Shing, J. Org. Chem. 1997, 62, 2622-2624.
73. K. Bowden, I. M. Heilbron, E. R. H. Jones, B. C. L. Weedon, J. Chem. Soc. 1946, 39-45.
74. CCDC 808455 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
75. S. L. Huang, D. Swern, J. Org. Chem. 1978, 43, 4537-4538
76. S. L. Huang, D. Swern, Tetrahedron 1978, 34, 1651-1660.
77. CCDC 808451 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
78. P. R. Khoury, J. D. Goddard, W. Tam, Tetrahedron 2004, 60, 8103-8112.
79. Recent theoretical calculations revealed an additional, non-electrocyclic ring opening pathway, see:, C. A. Sader, K. N. Houk, J. Org. Chem. 2012, 77, 4939-4948.
80. Z. Benko, B. Fraser-Reid, J. Org. Chem. 1988, 53, 2066-2072
81. T. Yamashita, J. Org. Chem. 1996, 61, 6438-6441; for a review, see
82. G. S. C. Srikanth, S. L. Castle, Tetrahedron 2005, 61, 10377-10441.
83. For a comprehensive review on [3,3]-sigmatropic rearrangements, see:, A. M. Martín Castro, Chem. Rev. 2004, 104, 2939-3002.
84. H. L. Goering, C. C. Tseng, J. Org. Chem. 1983, 48, 3986-3990
85. H. L. Goering, S. S. Kanter, C. C. Tseng, J. Org. Chem. 1983, 48, 715-721.
86. J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron Lett. 1966, 7, 3353-3354
87. J. Furukawa, N. Kawabata, J. Nishimura, Tetrahedron 1968, 24, 53-58.
88. Z. Yang, J. C. Lorenz, Y. Shi, Tetrahedron Lett. 1998, 39, 8621-8624
89. J. C. Lorenz, J. Long, Z. Yang, S. Xue, Y. Xie, Y. Shi, J. Org. Chem. 2004, 69, 327-334.
90. W. von E. Doering, P. LaFlamme, J. Am. Chem. Soc. 1956, 78, 5447-5448.
91. T. Aoyama, Y. Iwamoto, S. Nishigaki, T. Shioiri, Chem. Pharm. Bull. 1989, 37, 253-256
92. E. Vogel, W. Wiedmann, H. Kiefer, W. F. Harrison, Tetrahedron Lett. 1963, 4, 673-678
93. R. E. Pincock, J. I. Wells, J. Org. Chem. 1964, 29, 965-967.
94. N. G. Rondan, K. N. Houk, J. Am. Chem. Soc. 1985, 107, 2099-2111, and ref. therein
95. B. K. Carpenter, Tetrahedron 1978, 34, 1877-1884
96. S. Niwayama, E. A. Kallel, D. C. Spellmeyer, C. Sheu, K. N. Houk, J. Org. Chem. 1996, 61, 2813-2825.
97. R. B. Woodward, R. Hoffmann, Angew. Chem. 1969, 81, 797-869
98. Angew. Chem. Int. Ed. Engl. 1969, 8, 781-853.
99. For a review, see:, W. J. Leigh, Chem. Rev. 1993, 93, 487-505.
100. K. C. Bishop III, Chem. Rev. 1976, 76, 461-486
101. F. D. Mango, Coord. Chem. Rev. 1975, 15, 109-205
102. R. Pettit, H. Sugahara, J. Wristers, W. Merk, Discuss. Faraday Soc. 1969, 47, 71-78.
103. W. Slegeir, R. Case, J. S. McKennis, R. Pettit, J. Am. Chem. Soc. 1974, 96, 287-288; see also
104. W. Grimme, E. Schneider, Angew. Chem. 1977, 89, 754-756
105. Angew. Chem. Int. Ed. Engl. 1977, 16, 717-718
106. W. Grimme, H. G. Köser, J. Am. Chem. Soc. 1981, 103, 5919-5920.
107. M. Nitta, H. Miyano, T. Kobayashi, Heterocycles 1986, 24, 77-85
108. S. Araki, E. Bonfantini, P. Vogel, Helv. Chim. Acta 1988, 71, 1354-1366.
109. S. V. Ley, C. M. R. Low, A. D. White, J. Organomet. Chem. 1986, 302, C 13 -C 16.
110. H.-J. Knölker, G. Baum, N. Foitzik, H. Goesmann, T. Gonser, P. G. Jones, H. Röttele, Eur. J. Inorg. Chem. 1998, 993-1007
111. H.-J. Knölker, B. Ahrens, P. Gonser, M. Heiniger, P. G. Jones, Tetrahedron 2000, 56, 2259-2271.
112. M. Ochiai, S. Iwaki, T. Ukita, Y. Nagao, Chem. Lett. 1987, 133-134
113. D. Le Goanvic, M. A. Tius, J. Org. Chem. 2006, 71, 7800-7804.
114. T. Nishimura, K. Ohe, S. Uemura, J. Am. Chem. Soc. 1999, 121, 2645-2646.
115. M. Lj. Mihailović, M. Jakovljević, Ž. Čeković, Tetrahedron 1969, 25, 2269-2273
116. M. Lj. Mihailović, L. Lorenc, M. Gašić, M. Rogić, A. Melera, M. Stafanović, Tetrahedron 1966, 22, 2345-2358.
117. CCDC 808456 and -808453 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
118. W. Nagata, M. Yoshioka, S. Hirai, J. Am. Chem. Soc. 1972, 94, 4635-4643.
119. CCDC 808452 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
120. Y. Yamamoto, S. Yamamoto, H. Yatagai, Y. Ishihara, K. Maruyama, J. Org. Chem. 1982, 47, 119-126.
121. C. Petrier, J. C. De Souza Barbosa, C. Dupuy, J.-L. Luche, J. Org. Chem. 1985, 50, 5761-5765
122. A. E. Greene, J.-P. Lansard, J.-L. Luche, C. Petrier, J. Org. Chem. 1984, 49, 931-932.
123. E. C. Ashby, G. Heinsohn, J. Org. Chem. 1974, 39, 3297-3299
124. S. Flemming, J. Kabbara, K. Nickisch, H. Neh, J. Westermann, Synthesis 1995, 317-320.
125. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353-1364; for a reviews, see
126. A.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341-2372
127. Y. G. Gololobov, A. N. Nesmeyano, V. P. Lysenko, I. E. Boldeskul, Tetrahedron 1987, 43, 2609-2651.
128. W. G. Dauben, E. J. Deviny, Org. Chem. 1966, 31, 3794-3798.
129. S. Kim, K. H. Ahn, J. Org. Chem. 1984, 49, 1717-1724.
130. CCDC 785390 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
131. R. Hara, T. Furukawa, H. Kashima, H. Kusama, Y. Horiguchi, I. Kuwajima, J. Am. Chem. Soc. 1999, 121, 3072-3082.
132. For a comprehensive overview of methods to oxidized adjacent to C=O bonds, see:, D. R. Buckle, I. L. Pinto, in Comprehensive Organic Synthesis Volume 7 (Eds.:, B. M. Trost, I. Fleming,), Pergamon Press, Oxford, 1991, pp. 119-149.
133. CCDC 808454 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
134. For a review of acyl anion equivalents, see:, R. A. Aitken, A. W. Thomas, Adv. Heterocycl. Chem. 2001, 79, 89-114.
135. S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750-751.
136. E. Kaspar, R. Wiechert, Chem. Ber. 1958, 91, 2664-2670.
137. J. Hooz, R. B. Layton, J. Am. Chem. Soc. 1971, 93, 7320-7322.
138. P. A. Jacobi, S. Murphree, F. Ruprecht, W. Zheng, J. Org. Chem. 1996, 61, 2413-2427.
139. F. P. Ballistreri, S. Failla, E. Spina, G. A. Tomaselli, J. Org. Chem. 1989, 54, 947-949.
140. R. M. Moriarty, R. Penmasta, A. K. Awasthi, I. Prakash, J. Org. Chem. 1988, 53, 6124-6125.
141. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
142. D. Yang, F. Chen, Z.-M. Dong, D.-W. Zhang, J. Org. Chem. 2004, 69, 2221-2223
143. X.-W. Chang, D.-W. Zhang, F. Chen, Z.-M. Dong, D. Yang, Synlett 2009, 3159-3162.
144. J. K. Cha, W. J. Christ, Y. Kishi, Tetrahedron Lett. 1983, 24, 3943-3946.
145. N. K. Dunlap, M. R. Sabol, D. S. Watt, Tetrahedron Lett. 1984, 25, 5839-5842.
146. E. Nakamura, T. Inubushi, S. Aoki, D. Machii, J. Am. Chem. Soc. 1991, 113, 8980-8982.
147. P. Caramella, N. G. Rondan, M. N. Paddon-Row, K. N. Houk, J. Am. Chem. Soc. 1981, 103, 2438-2440.