Synthesis of heterocyclic systems by transition-metal-catalyzed cyclization-migration reactions - A diversity-oriented strategy for the construction of spirocyclic 3(2H)-furanones and 3-pyrrolones

European Journal of Organic Chemistry

Volumn , Issue 10, 2007, Pages 1636-1647

  Binder, Jörg T ^a   Crone, Benedikt ^a   Kirsch, Stefan F ^a   Liébert, Clémence ^a   Menz, Helge ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cyclizations; Domino reactions; Gold; Heterocycles; Platinum

Indexed keywords

EID: 34250614357     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601060     Document Type: Article

References (214)

1. a) L. E. Overman, L. D. Pennington, J. Org. Chem. 2003, 68, 7143-7157;
2. b) L. E. Overman, Acc. Chem. Res. 1992, 25, 352-359.
3. For selected reviews, see: a) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344;
4. Angew. Chem. Int. Ed. 2006, 45, 7134-7186;
5. b) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
6. c) S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137-166;
7. d) G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338;
8. e) L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170;
9. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
10. a) H. Menz, S. F. Kirsch, Org. Lett. 2006, 8, 4795-4797;
11. b) J. T. Binder, S. F. Kirsch, Org. Lett. 2006, 8, 2151-2153;
12. c) M. H. Suhre, M. Reif, S. F. Kirsch, Org. Lett. 2005, 7, 3925-3927.
13. For leading references, see: a) D. S. Tan, Nat. Chem. Biol. 2005, 1, 74-84;
14. b) A. B. Beeler, S. E. Schaus, J. A. Porco Jr, Curr. Opin. Chem. Biol. 2005, 9, 277-284;
15. c) M. D. Burke, E. M. Berger, S. L. Schreiber, J. Am. Chem. Soc. 2004, 126, 14095-14104;
16. d) K. Young-kwon, A. A. Midori, A. Takayoshi, J. O. Lamenzo, E. F. Dean, N. Patterson, P. A. Clemons, S. L. Schreiber, J. Am. Chem. Soc. 2004, 126, 14740-14745;
17. e) M. D. Burke, S. L. Schreiber, Angew. Chem. 2003, 116, 48-60;
18. Angew. Chem. Int. Ed. 2003, 43, 46-58;
19. f) M. D. Burke, E. M. Berger, S. L. Schreiber, Science 2003, 302, 613-618;
20. g) E. A. Couladouros, A. T. Strongilos, Angew. Chem. 2002, 114, 3829-3832;
21. Angew. Chem. Int. Ed. 2002, 41, 3677-3680;
22. h) S. L. Schreiber, Science 2000, 287, 1964-1969.
23. For recent examples, see inter alia: a) A. R. Yeager, G. K. Min, J. A. Porco Jr, S. E. Schaus, Org. Lett. 2006, 8, 5065-5068;
24. b) N. Kumar, M. Kiuchi, J. A. Tallarico, S. L. Schreiber, Org. Lett. 2005, 7, 2535-2538.
25. a) A. Fürstner, Angew. Chem. 2003, 115, 3706-3728;
26. Angew. Chem. Int. Ed. 2003, 42, 3582-3603;
27. b) J. R. Liddell, Nat. Prod. Rep. 2002, 19, 773-781;
28. c) D. O. Hagan, Nat. Prod. Rep. 2000, 17, 435-446;
29. d) D. L. Boger, C. W. Boyce, M. A. Labroli, C. A. Sehon, Q. Jin, J. Am. Chem. Soc. 1999, 121, 54-62;
30. e) R. J. Sundberg, in: Comprehensive Heterocyclic Chemistry II, vol. 2 (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Elsevier, Oxford, 1996, p. 119.
31. a) X. L. Hou, Z. Yang, H. N. C. Wong, in: Progress in Heterocyclic Chemistry, vol. 15 (Eds.: G. W. Gribble, T. L. Gilchrist), Pergamon, Oxford, 2003, p. 167-205;
32. b) D. M. X. Donnelly, M. J. Meegan, in: Comprehensive Heterocyclic Chemistry, vol. 4 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, p. 657-712;
33. c) B. H. Lipshutz, Chem. Rev. 1986, 86, 795-819;
34. d) F. A. Dean, Naturally Occurring Oxygen Ring Compounds, Butterworth, London, 1963;
35. e) F. Q. Alali, X.-X. Liu, J. L. McLaughlin, J. Nat. Prod. 1999, 62, 504-540.
36. For recent reviews, see: a) S. F. Kirsch, Org. Biomol. Chem. 2006, 4, 2076-2080;
37. b) R. C. D. Brown, Angew. Chem. 2005, 117, 872-874;
38. Angew. Chem. Int. Ed. 2005, 44, 850-852;
39. c) G. Balme, Angew. Chem. 2004, 116, 6396-6399;
40. Angew. Chem. Int. Ed. 2004, 43, 6238-6241;
41. d) B. Gabriele, G. Salerno, M. Costa, Synlett 2004, 2468-2483.
42. For selected examples, see: a) O. V. Larionov, A. de Meijere, Angew. Chem. 2005, 117, 5809-5813;
43. Angew. Chem. Int. Ed. 2005, 44, 5664-5667;
44. b) Y. Yamamoto, H. Hayashi, T. Saigoku, H. Nishiyama, J. Am. Chem. Soc. 2005, 127, 10804-10805;
45. c) D. Suzuki, Y. Nobe, Y. Watai, R. Tanaka, Y. Takayama, F. Sato, H. Urabe, J. Am. Chem. Soc. 2005, 127, 7474-7479;
46. d) S. Kamijo, C. Kanazawa, Y. Yamamoto, J. Am. Chem. Soc. 2005, 127, 9260-9266;
47. e) D. Tejedor, D. González-Cruz, A. Santos-Expósito, J. J. Marrero-Tellado, P. de Armas, F. García-Tellado, Chem. Eur. J. 2005, 11, 3502-3510;
48. f) R. Dhawan, B. A. Arndtsen, J. Am. Chem. Soc. 2004, 126, 468-469;
49. g) C.-K. Jung, J.-C. Wang, M. J. Krische, J. Am. Chem. Soc. 2004, 126, 4118-4119;
50. h) X. Han, R. A. Widenhoefer, J. Org. Chem. 2004, 69, 1738-1740;
51. i) A. W. Sromek, A. V. Kel'in, V. Gevorgyan, Angew. Chem. 2004, 116, 2330-2332;
52. Angew. Chem. Int. Ed. 2004, 43, 2280-2282;
53. j) D. Tejedor, F. García-Tellado, J. J. Marrero-Tellado, P. de Armas, Chem. Eur. J. 2003, 9, 3122-3131;
54. k) S. Ma, J. Zhang, L. Lu, Chem. Eur. J. 2003, 9, 2447-2456.
55. For reviews, see: a) C. Bruneau, Angew. Chem. 2005, 117, 2380-2386;
56. Angew. Chem. Int. Ed. 2005, 44, 2328-2334;
57. b) A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436;
58. c) M. Méndez, V. Mamane, A. Fürstner, Chemtracts 2003, 16, 397;
59. d) M. Meńdez, A. M. Echavarren, Eur. J. Org. Chem. 2002, 15-28.
60. For leading references on alkene activation, see: a) C. Brouwer, C. He, Angew. Chem. 2006, 118, 1776-1779;
61. Angew. Chem. Int. Ed. 2006, 45, 1744-1747;
62. b) C.-G. Yang, C. He, J. Am. Chem. Soc. 2005, 127, 6966-6967;
63. c) C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2005, 127, 1070-1071.
64. For selected references on gold-catalyzed alkyne activation, see: a) J. Sun, M. P. Conley, L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 9705-9710;
65. b) C. Ferrer, A. M. Echavarren, Angew. Chem. 2006, 118, 1123-1127;
66. Angew. Chem. Int. Ed. 2006, 45, 1105-1109;
67. c) J. Barluenga, A. Diéguez, A. Fernández, F. Rodriguez, F. J. Fañanás, Angew. Chem. 2006, 118, 2145-2147;
68. Angew. Chem. Int. Ed. 2006, 45, 2091-2093;
69. d) N. Marion, S. Díez-González, P. de Frémont, A. R. Noble, S. P. Nolan, Angew. Chem. 2006, 118, 3729-3732;
70. Angew. Chem. Int. Ed. 2006, 45, 3647-3650;
71. e) P. Dube, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 12062-12063;
72. f) E. Genin, P. Y. Toullec, S. Antoniotti, C. Brancour, J.-P. Genet, V. Michelet, J. Am. Chem. Soc. 2006, 128, 3112-3113;
73. g) D. Hildebrandt, G. Dyker, J. Org. Chem. 2006, 71, 6728-6733;
74. h) T. J. Harrison, J. A. Kozak, M. Corbella-Pane, G. R. Dake, J. Org. Chem. 2006, 71, 4525-4529;
75. i) A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515-518;
76. j) A. Fürstner, P. Hannen, Chem. Eur. J. 2006, 12, 3006-3019;
77. k) C. Nieto-Oberhuber, S. López, M. P. Muñoz, E. Jiménez-Núñez, E. Buñuel, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1694-1702;
78. l) A. S. K. Hashmi, R. Salathé, W. Frey, Chem. Eur. J. 2006, 12, 6991-6996;
79. m) A. S. K. Hashmi, J. P. Weyrauch, E. Kurpejovic, T. M. Frost, B. Miehlich, W. Frey, J. W. Bats, Chem. Eur. J. 2006, 12, 5806-5814;
80. n) A. S. K. Hashmi, M. Rudolph, J. P. Weyrauch, M. Wölfle, W. Frey, J. W. Bats, Angew. Chem. 2005, 117, 2858-2861;
81. Angew. Chem. Int. Ed. 2005, 44, 2798-2801;
82. o) M. J. Johansson, D. J. Gorin, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 18002-18003;
83. p) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2005, 127, 6962-6963:
84. q) X. Shi, D. J. Gorin, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 5802-5803;
85. r) C. Nevado, A. M. Echavarren, Chem. Eur. J. 2005, 11, 3155-3164;
86. s) C. Nieto-Oberhuber, M. Paz Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
87. Angew. Chem. Int. Ed. 2004, 43, 2402-2406;
88. t) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 11806-11807;
89. u) A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11553-11554.
90. For leading references on platinum-catalyzed alkyne activation, see: a) B. G. Pujanauski, B. A. Bhanu Prasad, R. Sarpong, J. Am. Chem. Soc. 2006, 128, 6786-6787;
91. b) A. Fürstner, C. Aissa, J. Am. Chem. Soc. 2006, 128, 6306-6307;
92. c) A. Fürstner, P. W. Davies, J. Am. Chem. Soc. 2005, 127, 15024-15025;
93. d) A. Fürstner, P. W. Davies, T. Gress, J. Am. Chem. Soc. 2005, 127, 8244-8245;
94. e) B. A. Bhanu Prasad, F. K. Yoshimoto, R. Sarpong, J. Am. Chem. Soc. 2005, 127, 12468-12469;
95. f) A. S. K. Hashmi, J. P. Weyrauch, M. Rudolph, E. Kurpejovi, Angew. Chem. 2004, 116, 6707-6709;
96. Angew. Chem. Int. Ed. 2004, 43, 6545-6547;
97. g) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655;
98. h) T. J. Harrison, G. R. Dake, Org. Lett. 2004, 6, 5023-5026;
99. i) F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509-1511;
100. j) B. Martin-Matute, C. Nevado, D. J. Cardenas, A. M. Echavarren, J. Am. Chem. Soc. 2003, 125, 5757-5766;
101. k) M. Mendez, M. P. Munoz, C. Nevado, D. J. Cardenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10511-10520.
102. For reviews on gold-catalyzed reactions, see: a) S. Ma, S. Yu, Z. Gu, Angew. Chem. 2005, 118, 206-209;
103. Angew. Chem. Int. Ed. 2005, 45, 200-203;
104. b) A. S. K. Hashmi, Angew. Chem. 2005, 117, 7150-7154;
105. Angew. Chem. Int. Ed. 2005, 44, 6990-6993;
106. c) A. Hoffmann-Röder, N. Krause, Org. Biomol. Chem. 2005, 3, 387-391;
107. d) A. Arcadi, S. D. Giuseppe, Curr. Org. Chem. 2004, 8, 795-812;
108. e) A. S. K. Hashmi, Gold Bull. 2004, 37, 51-65;
109. f) A. S. K. Hashmi, Gold Bull. 2003, 36, 3-9;
110. g) G. Dyker, Angew. Chem. 2000, 112, 4407-4409;
111. Angew. Chem. Int. Ed. 2000, 39, 4237-4239.
112. For the construction of heterocycles by noble-metal-catalyzed skeletal reorganization, see inter alia: a) V. Belting, N. Krause, Org. Lett. 2006, 8, 4489-4492;
113. b) X. Han, R. A. Widenhoefer, Angew. Chem. 2006, 118, 1779-1781;
114. Angew. Chem. Int. Ed. 2006, 45, 1747-1749;
115. c) N. Morita, N. Krause, Angew. Chem. 2006, 118, 1930-1933;
116. Angew. Chem. Int. Ed. 2006, 45, 1897-1899;
117. d) Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073;
118. e) X. Yao, C.-J. Li, Org. Lett. 2006, 8, 1953-1955;
119. f) B. Gockel, N. Krause, Org. Lett. 2006, 8, 4485-4488;
120. g) Y. Liu, M. Liu, S. Guo, H. Tu, Y. Zhou, H. Gao, Org. Lett. 2006, 8, 3445-3448;
121. h) A. W. Sromek, M. Rubina, V. Gevorgyan, J. Am. Chem. Soc. 2005, 127, 10500-10501;
122. i) D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 11260-11261;
123. j) M. Alfonsi, A. Arcadi, M. Aschi, G. Bianchi, F. Marinelli, J. Org. Chem. 2005, 70, 2265-2273;
124. k) Y. Liu, F. Song, Z. Song, M. Liu, B. Yan, Org. Lett. 2005, 7, 5409-5412;
125. l) N. Morita, N. Krause, Org. Lett. 2004, 6, 4121-4123;
126. m) A. S. K. Hashmi, J. P. Weyrauch, W. Frey, J. W. Bats, Org. Lett. 2004, 6, 4391-4394;
127. n) N. Krause, A. Hoffmann-Röder, J. Canisius, Synthesis 2002, 1759-1774;
128. o) A. Hoffmann-Röder, N. Krause, Org. Lett. 2001, 3, 2537-2538.
129. a) T. Yao, X. Zhang, R. C. Larock, J. Org. Chem. 2005, 70, 7679-7685;
130. b) T. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 11164-11165.
131. a) X. Liu, Z. Pan, X. Shu, X. Duan, Y. Liang, Synlett 2006, 1962-1964;
132. b) N. T. Patil, H. Wu, Y. Yamamoto, J. Org. Chem. 2005, 70, 4531-4534.
133. For related cyclizations, see: a) A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost, Angew. Chem. 2000, 112, 2382-2385;
134. Angew. Chem. Int. Ed. 2000, 39, 2285-2288;
135. b) A. S. K. Hashmi, T. L. Ruppert, T. Knofel, J. W. Bats, J. Org. Chem. 1997, 62, 7295-7304;
136. c) A. S. K. Hashmi, Angew. Chem. 1995, 107, 1749-1751;
137. Angew. Chem. Int. Ed. Engl. 1995, 34, 1581-1583;
138. d) J. A. Marshall, C. A. Sehon, J. Org. Chem. 1995, 60, 5966-5968;
139. e) J. A. Marshall, E. M. Wallace, P. S. Coan, J. Org. Chem. 1995, 60, 796-797;
140. f) J. A. Marshall, X. J. Wang, J. Org. Chem. 1992, 57, 3387-3396;
141. g) J. A. Marshall, X. J. Wang, J. Org. Chem. 1991, 56, 960-969;
142. [15g]
143. For recent examples of gold-catalyzed domino processes, see: a) A. Buzas, F. Gagosz, J. Am. Chem. Soc. 2006, 128, 12614-12615;
144. b) J. Zhao, C. O. Hughes, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 7436-7437;
145. c) E. Jiménez-Núñez, C. K. Claverie, C. Nieto-Oberhuber, A. M. Echavarren, Angew. Chem. 2006, 118, 5578-5581;
146. Angew. Chem. Int. Ed. 2006, 45, 5452-5455;
147. d) I. V. Seregin, V. Gevorgyan, J. Am. Chem. Soc. 2006, 128, 12050-12051;
148. e) C. Nieto-Oberhuber, S. López, E. Jiménez- Núñez, A. M. Echavarren, Chem. Eur. J. 2006, 12, 5916-5923;
149. f) J. Zhang, H.-G. Schmalz, Angew. Chem. 2006, 118, 6856-6859;
150. Angew. Chem. Int. Ed. 2006, 45, 6704-6707;
151. g) A. L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804-16805;
152. h) A. S. K. Hashmi, L. Grundl, Tetrahedron 2005, 61, 6231-6236.
153. a) Y. Nagao, S. Tanaka, A. Ueki, M. Kumazawa, S. Goto, T. Ooi, S. Sano, M. Shiro, Org. Lett. 2004, 6, 2133-2136;
154. b) R. E. Hartung, D. G. Hilmey, L. A. Paquette, Adv. Synth. Catal. 2004, 346, 713-716;
155. c) L. A. Paquette, J. E. Hofferberth, Org. React. 2003, 62, 477;
156. d) H. Brunner, H. B. Kagan, G. Kreutze, Tetrahedron: Asymmetry 2003, 14, 2177-2187;
157. e) H. Brunner, F. Stöhr, Eur. J. Org. Chem. 2000, 2777-2786.
158. a) J. P. Markham, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 9708-9709;
159. b) B. M. Trost, D. C. Lee, J. Am. Chem. Soc. 1988, 110, 6556-6558;
160. c) M. Sworin, W. L. Neumann, J. Org. Chem. 1988, 53, 4894-4896;
161. d) T. Sano, J. Toda, Y. Tsuda, Heterocycles 1984, 22, 53-58.
162. Parts of this study have been published in preliminary form, see: S. F. Kirsch, J. T. Binder, C. Liébert, H. Menz, Angew. Chem. 2006, 118, 6010-6013;
163. Angew. Chem. Int. Ed. 2006, 118, 5878-5880.
164. a) P. K. Dhondi, J. D. Chisholm, Org. Lett. 2006, 8, 67-69;
165. b) B. Jiang, Z. Chen, X. Tang, Org. Lett. 2002, 4, 3451-3453.
166. M. Yamaguchi, I. Hirao, Tetrahedron Lett. 1983, 24, 391-394.
167. For the synthesis of IBX, see: a) C. Hartmann, V. Meyer, Ber. Dtsch. Chem. Ges. 1893, 26, 1727-1732;
168. b) M. Frigerio, M. Santagostino, S. Sputore, J. Org. Chem. 1999, 64, 4537-4538.
169. S. F. Kirsch, J. Org. Chem. 2005, 70, 10210-10212.
170. B. Crone, S. F. Kirsch, Chem. Commun. 2006, 764-766.
171. a) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, J. Am. Chem. Soc. 2000, 122, 7596-7597;
172. b) K. C. Nicolaou, T. Montagnon, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2245-2258;
173. c) K. C. Nicolaou, T. Montagnon, P. S. Baran, Angew. Chem. 2002, 114, 1038-1042;
174. Angew. Chem. Int. Ed. 2002, 41, 993-996;
175. d) K. C. Nicolaou, D. L. F. Gray, T. Montagnon, S. T. Harrison, Angew. Chem. 2002, 114, 1444-1447;
176. Angew. Chem. Int. Ed. 2002, 41, 996-1000.
177. In the case of 4q, 2-(2-phenylethynyl)cycloheptanone was isolated in 77% yield (3.0 equiv. IBX, 24 h, 23°C, DMSO).
178. K. Kaneda, K. Jitsukawa, T. Itoh, S. Teranishi, J. Org. Chem. 1980, 45, 3004-3009.
179. 3CN, 15 mL/ min, 254 nm.
180. P. W. Le Quesne, S. B. Levery, M. D. Menachery, T. F. Brennan, R. F. Raffauf, J. Chem. Soc. Perkin Trans. 1 1978, 1572-1580.
181. a) A. B. Smith III, M. A. Guaciaro, S. R. Schow, P. M. Wovkulich, B. H. Toder, T. W. Hall, J. Am. Chem. Soc. 1981, 103, 219-222;
182. b) S. M. Kupchan, C. W. Sigel, M. J. Matz, C. J. Gilmore, R. F. Bryan, J. Am. Chem. Soc. 1976, 98, 2295-2300.
183. a) P. J. Jerris, A. B. Smith III, J. Org. Chem. 1981, 46, 577-585;
184. b) D. L. Dreyer, A. Lee, Phytochemistry 1972, 11, 763-767.
185. S. S. Shin, Y. Byun, K. M. Lim, J. K. Choi, K.-W. Lee, J. H. Moh, J. K. Kim, Y. S. Jeong, J. Y. Kim, Y. H. Choi, H.-J. Koh, Y.-H. Park, Y. I. Oh, M.-S. Noh, S. Chung, J. Med. Chem. 2004, 47, 792-804.
186. Y. Ishida, H. Tsuruta, S. T. Tsuneta, T. Uno, K. Watanabe, Y. Aizono, Biosci. Biotechnol. Biochem. 1998, 62, 2146-2150.
187. A. Carotti, A. Carried, S. Chimichi, M. Boccalini, B. Cosimelli, C. Gnerre, A. Carotti, P.-A. Carrupt, B. Testa, Bioorg. Med. Chem. Lett. 2002, 12, 3551-3555.
188. S. W. Felman, I. Jirkovsky, K. A. Memoli, L. Borella, C. Wells, J. Russell, J. Ward, J. Med. Chem. 1992, 35, 1183-1190.
189. a) X. Shao, C. Tamm, Tetrahedron Lett. 1991, 32, 2891-2892;
190. b) A. B. Smith III, P. A. Levenberg, P. J. Jerris, R. M. Scarborough Jr, P. M. Wovkulich, J. Am. Chem. Soc. 1981, 103, 1501-1513.
191. For synthetic equivalents of α′-hydroxy 1,3-diketones, see inter alia: a) S. Chimichi, M. Boccalini, B. Cosimelli, F. Dall'Acqua, G. Viola, Tetrahedron 2003, 59, 5215-5223;
192. b) S. Chimichi, M. Boccalini, B. Cosimelli, G. Viola, D, Vedaldi, F. Dall'Acqua, Tetrahedron Lett. 2002, 43, 7473-7476;
193. c) Y. Inoue, K. Ohuchi, S. Imaizumi, Tetrahedron Lett. 1988, 29, 5941-5942;
194. d) D. P. Curran, D. H. Singleton, Tetrahedron Lett. 1983, 29, 2079-2082.
195. a) J. Liu, M. Liu, S. Guo, H. Tu, Y. Zhou, H. Gao, Org. Lett. 2006, 8, 3445-3448;
196. b) M. Reiter, H. Turner, R. Mills-Webb, V. Gouverneur, J. Org. Chem. 2005, 70, 8478-8485;
197. c) J. E. Baldwin, R. C. Thomas, L. I. Kruse, L. Silberman, J. Org. Chem. 1977, 42, 3846-3852.
198. J. D. Winkler, K. Oh, S. M. Asselin, Org. Lett. 2005, 7, 387-389.
199. S. Sayama, Heterocycles 2005, 65, 1347-1358.
200. a) P. Sampson, V. Roussis, G. J. Drtina, F. L. Koerwitz, D. F. Wiemer, J. Org. Chem. 1986, 51, 2525-2529;
201. for similar cyclisation strategy, see: b) K. Kato, H. Nouchi, K. Ishikura, S. Takaishi, S. Motodate, H. Tanaka, K. Okudaira, T. Mochida, R. Nishigaki, K. Shigenobu, H. Akita, Tetrahedron Lett. 2006, 62, 2545-2554.
202. P. Langer, T. Krummel, Chem. Eur. J. 2001, 7, 1720-1727.
203. 3 is superior in terms of rate.
204. [15h]
205. a) H. Saimoto, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 1981, 103, 4975-4977;
206. b) W. Parker, R. A. Raphael, D. I. Wilkinson, J. Chem. Soc. 1958, 3871-3875.
207. S. Swaminathan, K. V. Narayanan, Chem. Rev. 1971, 71, 429-438.
208. When the alkynyl carbonyl compound was employed as a mixture of diastereomers, the diastereomeric products 13a and 13b were obtained in ratios identical to those of the starting material.
209. A. Arcadi, S. Di Giuseppe, F. Marinelli, E. Rossi, Adv. Synth. Catal. 2001, 343, 443-446.
210. a) H. McNab, L. C. Monahan, J. Chem. Soc., Perkin Trans. 1 1988, 869-873;
211. b) R. Ghaffari-Tabrizi, P. Margaretha, H. W. Schmalle, Helv. Chim. Acta 1984, 67, 1957-1962;
212. c) E. Immendorfer, Ber. Dtsch. Chem. Ges. 1915, 48, 605-616.
213. A. B. Smith III, S. D. Knight, P. A. Sprengeler, R. Hirschmann, Bioorg. Med. Chem. 1996, 4, 1021-1034.
214. M. Overhand, S. M. Hecht, J. Org. Chem. 1994, 59, 4721-4722.