Nitrenium ion azaspirocyclization-spirodienone cleavage: A new synthetic strategy for the stereocontrolled preparation of highly substituted lactams and N-hydroxy lactams

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10271-10284

  Wardrop, Duncan J ^a   Burge, Matthew S ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

1,4-CYCLOHEXADIENES; 2,5-CYCLOHEXADIENONES; DIASTEREOSELECTIVITY; NITRENIUM IONS;

AROMATIC COMPOUNDS;

1,4 CYCLOHEXADIENE; 2,5 CYCLOHEXADIENONE; ALKYL GROUP; AZETIDINONE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; LACTAM DERIVATIVE; PIPERIDONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRROLIDINE DERIVATIVE; SPIRO COMPOUND; SPIRODIENONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; INFRARED SPECTROSCOPY; OZONOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

AMIDES; CYCLIZATION; LACTAMS; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 28744444620     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051252r     Document Type: Article

References (173)

1. Ho, T.-L. Tactics of Organic Synthesis, 1st ed.; Wiley: New York, 1994; pp 50-53.
2. (a) Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. J. Am. Chem. Soc. 1954, 76, 4749.
3. (b) Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. Tetrahedron 1963, 19, 247.
4. For recent, representative reports concerning the oxidative degradation of benzenoid systems, see: (a) Audouard, C.; Barsukov, I.; Fawcett, J.; Griffith, G. A.; Percy, J. M.; Pintat, S.; Smith, C. A. Chem. Commun. 2004, 1526
5. (b) Lee, Y.-S.; Choung, W.-K.; Kim, K. H.; Kang, T. W.; Ha, D.-C. Tetrahedron 2004, 60, 867.
6. (c) Miranda, L. S. M.; Vasconcellos, M. L. A. A. Synthesis 2004, 1767.
7. (d) Demir, A.; Sesenoglu, O.; Ulku, D.; Arici, C. Helv. Chim. Acta 2003, 86, 91.
8. (e) Jaroch, S.; Holscher, P.; Rehwinkel, H.; Sulzle, D.; Burton, G.; Hillmann, M.; McDonald, F. M. Bioorg. Med. Chem. Lett. 2003, 13, 1981.
9. (f) Mander, L. N.; Williams, C. M. Tetrahedron 2003, 59, 1105 and references therein.
10. (g) Colletti, S. L.; Li, C.; Fisher, M. H.; Wyvratt, M. J.; Meinke, P. T. Tetrahedron Lett. 2000, 41, 7825.
11. (h) Bringmann, G.; Munchbach, M.; Michel, M. Tetrahedron: Asymmetry 2000, 11, 3167.
12. (i) Zhou, W.-S.; Lu, Z.-H.; Xu, Y.-M.; Liao, L.-X.; Wang, Z.-M. Tetrahedron 1999, 55, 11959.
13. Birch, A. J.; Fitton, F.; Smith, D. C. C.; Steere, D. E.; Stelfox, A. R. J. Chem. Soc. 1963, 2209.
14. (a) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1986, 27, 3119.
15. (b) Evans, D. A.; Gauchet-Prunet, J. A.; Carreira, E. M. and Charette, A. B. J. Org. Chem. 1991, 56, 741.
16. (c) Rao, A. V. R.; Gurjar, M. K.; Islam, A. Tetrahedron Lett. 1993, 34, 4993.
17. (a) Corey, E. J.; Katzenellenbogen, J. A.; Gilman, N. W.; Roman, S. A.; Erickson, B. W. J. J. Am. Chem. Soc. 1968, 90, 5618.
18. (b) Moody, C. J.; Toczek, J. Tetrahedron Lett. 1986, 27, 5253.
19. (c) Moody, C. J.; Toczek, J. J. Chem. Soc.-Perkin Trans. 1 1988, 1397.
20. (d) Kammler, R.; Polborn, K.; Wanner, K. T. Tetrahedron 2003, 59, 3359.
21. (a) Mittelbach, M.; Poklukar, N.; Junek, H. Liebigs Ann. Chem. 1990, 185.
22. (b) Bringmann, G.; Kuenkel, G.; Geuder, T. Synlett 1990, 253.
23. (c) Bringmann, G.; Geuder, T. Synthesis 1991, 829.
24. (a) Wipf, P.; Lim, S. J. Am. Chem. Soc., 1995, 117, 558.
25. (b) Wipf, P.; Reeves, J. T. Chem. Commun. 2002, 2066.
26. (c) Jung, I. C. Eur. J. Org. Chem. 2001, 1899.
27. (a) Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1 1995, 2509.
28. (b) Zvilichovsky, G.; Gurvich, V. J. Chem. Soc., Perkin Trans. 1 1997, 1069
29. (c) Zvilichovsky, G.; Gurvich, V. Tetrahedron 1995, 51, 5479.
30. (d) Gbara-Haj-Yahia, I.; Zvilichovsky, G.; Seri, N. J. Org. Chem. 2004, 69, 4135.
31. (a) Kirkemo, C. L.; White, J. D. J. Org. Chem., 1985, 50, 1316.
32. (b) Bringmann, G. Liebigs Ann., Chem. 1985, 2105.
33. For reports concerning the ozonolysis of 2,5-cyclohexadienones, see: (a) Caspi, E.; Schmid, W.; Khan, B. T. Tetrahedron 1962, 18, 767.
34. (b) Caspi, E.; Khan, B. T.; Balasubrahmanyam, S. N. Tetrahedron 1962, 78, 1013.
35. (c) Balasubrahmanyam, S. N.; Caspi, E.; Khan, B. T. J. Chem. Soc. 1963, 761.
36. (d) Rodig, O. R.; Zanati, G. J. Org. Chem. 1968, 33, 914.
37. (e) Okamoto, K.; Nitta, I.; Shingu, H. Bull. Chem. Soc. Jpn. 1970, 43, 1768.
38. (f) Bailey, P. S.; Ferrell, T. M. J. Org. Chem. 1981, 46, 5028.
39. (a) Harries, C.; Turk, H. Chem. Ber. 1905, 38, 1630.
40. (b) Harries, C. Ann. 1910, 374, 288.
41. (c) For an account of Harries' introduction of ozone into organic chemistry, see: Rubin, M. B. Helv. Chim. Acta 2003, 86, 930.
42. Bailey, P. S. Ozonation in Organic Chemistry, Vol. 1; Trahanovsky, W., Ed.; Academic Press: New York, 1978; Vol. I, pp 153-162.
43. Story, P. R.; Burgess, J. R. Tetrahedron Lett. 1968, 1287.
44. (a) Shibata, K.; Takegawa, S.; Koizumi, N.; Yamakoshi, N.; Shimazawa, E. Chem. Pharm. Bull. 1992, 40, 935.
45. (b) Koizumi, N.; Takegawa, S.; Mieda, M.; Shibata, K. Chem. Pharm. Bull. 1996, 44, 2162.
46. (c) Gambie, R. C.; Higgs, P. I.; Read, C. M.; Rutledge, P. S.; Ryan, G. R.; Woodgate, P. D. Aust. J. Chem. 1990, 43, 681.
47. For reviews covering the formation of quaternary stereogenic center, see: (a) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591.
48. (b) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388.
49. For recent reviews of phenolic oxidation, see: (a) Wirth, T. In Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis; Wirth, T., Ed.; Springer: Berlin, 2003; Vol. 224.
50. (b) Moriarty, R. M.; Prakash, O. Org. React. 2001, 57, 327.
51. (c) Pelter, A.; Ward, R. S. Tetrahedron 2001, 57, 273.
52. (a) Wardrop, D. J.; Basak, A. Org. Lett, 2001, 3, 1053.
53. (b) Wardrop, D. J.; Zhang, W. Org. Lett., 2001, 3, 2353.
54. (c) Wardrop, D. J.; Landrie, C. L.; Ortiz, J. A. Synlett, 2003, 1352.
55. For reviews concerning the chemistry of nitrenium ions, see: (a) Falvey, D. E. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Eds.; Wiley-Interscience: Hoboken, NJ, 2004; Chapter 13.
56. (b) Kikugawa, Y. Rev. Heteroatom Chem. 1996, 15, 263.
57. (c) Abramovitch, R. A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Eds.; Academic Press: Orlando, FL, 1984; Chapter 6.
58. For the intramolecular reaction acylnitrenium ions and related electron-deficient species with arenes, see: (a) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. J. Chem. Soc., Perkin Trans. 1 1984, 2255.
59. (b) Kikugawa, Y.; Kawase, M. J. Am. Chem. Soc. 1984, 706, 5728.
60. (c) Glover, S. A.; Goosen, A.; McCleland, C. W.; Schoonraad, J. L. Tetrahedron 1987, 43, 2577.
61. (d) Kawase, M.; Kitamura, T.; Kikugawa, Y. J. Org. Chem. 1989, 54, 3394.
62. (e) Cherest, M.; Lusinchi, X. Tetrahedron Lett. 1989, 30, 715.
63. (f) Glover, S. A.; Rowbottom, C. A.; Scott, A. P.; Schoonraad, J. L. Tetrahedron 1990, 46, 7247.
64. (g) Prata, J. V.; Clemente, D. T. S.; Prabhakar, S.; Lobo, A. M.; Mourato, I.; Branco, P. S. J. Chem. Soc., Perkin Trans. 1 2002, 513.
65. (h) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. Heterocycles 2003, 59, 149.
66. (i) Miyazawa, E.; Sakamoto, T.; Kikugawa, Y. J. Org. Chem. 2003, 68, 5429.
67. (j) Kikugawa, Y.; Nagashima, A.; Sakamoto, T.; Miyazawa, E.; Shiiya, M. J. Org. Chem. 2003, 68, 6739.
68. Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron. Lett., 2003, 44, 2587.
69. Sakai, R.; Oiwa, C.; Takaishi, K.; Kamiya, H.; Tagawa, M. Tetrahedron Lett. 1999, 40, 6941.
70. For syntheses of dysibetaine, see: (a) Langlois, N.; Le Nguyen, B. K. J. Org. Chem. 2004, 69, 7558.
71. (b) Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2003, 44, 5961.
72. (c) Snider, B. B.; Gu, Y. Org. Lett. 2001, 3, 1761.
73. (a) Shin-ya, K.; Kim, J. S.; Furihata, K.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1997,38, 7079.
74. (b) Okue, M.; Kobayashi, H.; Shinya, K.; Furihata, K.; Hayakawa, Y.; Seto, H.; Watanabe, H.; Kitahara, T. Tetrahedron Lett. 2002, 43, 857.
75. Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355.
76. (a) Gordon, E. M.; Ondetti, M. A.; Pluscec, J.; Cimarusti, C. M.; Bonner, D. P.; Sykes, R. B. J. Am. Chem. Soc. 1982, 104, 6053.
77. (b) Koster, W. H.; Bonner, D. P. In Frontiers of Antibiotic Research; Umezawa, H., Ed.; Academic Press: New York, 1987; p 211
78. Wardrop, D. J.; Burge, M. S. Chem. Commun. 2004, 1230.
79. (a) Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1976, 41, 1396.
80. (b) Keul, H.; Kuczkowski, R. L. J. Am. Chem. Soc. 1984, 106, 5370.
81. (c) Keul, H.; Kuczkowski, R. L.; Choi, H.-S. J. Org. Chem. 1985, 50, 3365.
82. (d) Wojciechowski, B. J.; Pearson, W. H.; Kuczkowski, R. L. J. Org. Chem. 1989, 54, 115.
83. (e) Griesbaum, K.; Kim, W. S.; Nakamura, N.; Mori, M.; Nojima, M.; Kusabayashi, S. J. Org. Chem. 1990, 55, 6153.
84. (f) Bunnelle, W. H. Chem. Rev. 1991, 91, 335.
85. (g) Griesbaum, K.; Kim, W. S. J. Org. Chem. 1992, 57, 5574.
86. (h) Killers, S.; Niklaus, A.; Reiser, O. J. Org. Chem. 1993, 58, 3169.
87. (i) Schank, K.; Beck, H.; Pistorius, S. Helv. Chim. Acta 2004, 87, 2025.
88. For reports of the efficient ozonolysis of dihydropyrones, see: (a) Danishefsky, S.; Kato, N.; Askin, D.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1982, 104, 360.
89. (b) Sugiyama, T.; Yamakoshi, H.; Nojima, M. J. Org. Chem. 1993, 58, 4212.
90. For details of the preparation of 10, see the Supporting Information.
91. 2, in the absence of methanol (entries 2 and 3). Diagram presented
92. (b) Nilsson, A.; Ronlán, A.; Parker, V. D. Tetrahedron Lett. 1975, 1107.
93. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
94. Analogous rationalizations of π-facial diastereoselectivity are proposed in: (a) Wender, P. A.; Ternansky, R. J. Tetrahedron Lett. 1985, 26, 2625.
95. (b) Adam, W.; Peters, E. M.; Peters, K.; Prein, M.; von Schnering, H. G. J. Am. Chem. Soc. 1995, 117, 6686.
96. (c) Kamikawa, K.; Furusyo, M.; Uno, T.; Sato, Y.; Konoo, A.; Bringmann, G.; Uemura, M. Org. Lett. 2001, 3, 3667.
97. 2-S cyclization of 3-substituted 3-aryl-1-benzyloxyureas has previously been noted: Romero, A. G.; Darlington, W. H.; Jacobsen, E. J.; Mickelson, J. W. Tetrahedron Lett. 1996, 37, 2361 (footnote 7).
98. For examples of biologically active N-hydroxy lactams and their derivatives, see: (a) Higashide, E.; Horii, S.; Ono, H.; Mizokami, N.; Yamazaki, T.; Shibata, M.; Yoneda, M. J. Antibiot. 1985, 38, 285.
99. (b) Schlemminger, I.; Mole, D. R.; McNeill, L. A.; Dhanda, A.; Hewitson, K. S.; Tian, Y. M.; Ratcliffe, P. J.; Pugh, C. W.; Schofield, C. J. Bioorg. Med. Chem. Lett. 2003, 13, 1451.
100. (c) Wendenbaum, S.; Demange, P.; Dell, A.; Meyer, J. M.; Abdallah, M. A. Tetrahedron Lett. 1983, 24, 4877.
101. (d) Swarén, P.; Massova, I.; Bellettini, J. R.; Bulychev, A.; Maveyraud, L.; Kotra, L. P.; Miller, M. J.; Mobashery, S.; Samama, J. P. J. Am. Chem. Soc. 1999, 121, 5353.
102. (e) Bulychev, A.; O'Brien, M. E.; Massova, I.; Teng, M.; Gibson, T. A.; Miller, M. J.; Mobashery, S. J. Am. Chem. Soc. 1995, 117, 5938.
103. (f) Bulychev, A.; Bellettini, J. R.; O'Brien, M.; Crocker, P. J.; Samama, J.-P.; Miller, M. J.; Mobashery, S. Tetrahedron 2000, 56, 5719.
104. Schreiber, S. L.; Claus, R. E.; Reagan, J. Tetrahedron Lett. 1982, 23, 3867.
105. Gupta, D.; Soman, R.; Dev, S. Tetrahedron 1982, 38, 3013.
106. Duhamel, P.; Kotera, M.; Monteil, T.; Marabout, B.; Davoust, D. J. Org. Chem. 1989, 54, 4419.
107. The instablity of related systems to basic conditions has been noted: (a) Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230.
108. (b) Trancard, D.; Tout, J.-B.; Giard, T.; Chichaoui, I.; Cahard, D.; Plaquevent, J.-C. Tetrahedron Lett. 2000, 41, 3843.
109. (c) Duhamel, P.; Kotera, M. J. Org. Chem. 1982, 47, 1688.
110. Bis(hydroxymethyl)pyrrolidinones and their derivatives are of interest as neuraminidase inhibitors: (a) Brouillette, W. J.; Bajpai, S. N.; Ali, S. M.; Velu, S. E.; Atigadda, V. R.; Lommer, B. S.; Finley, J. B.; Luo, M.; Air, G. M. Bioorg. Med. Chem. 2003, 11, 2739.
111. (b) Schieweck, F.; Altenbach, H. J. J. Chem. Soc., Perkin Trans. 1 2001, 3409.
112. (c) Atigadda, V. R.; Brouillette, W. J.; Duarte, F.; Ali, S. M.; Babu, Y. S.; Bantia, S.; Chand, P.; Chu, N.; Montgomery, J. A.; Walsh, D. A.; Sudbeck, E. A.; Finley, J.; Luo, M.; Air, G. M.; Laver, G. W. J. Med. Chem. 1999, 42, 2332.
113. (a) Ishmuratov, G. Y.; Kharisov, R. Y.; Yakovleva, M. P.; Botsman, O. V.; Muslukhov, R. R.; Tolstikov, G. A. Russ. J. Org. Chem. 2001, 37, 37.
114. (b) Gribble, G. W. Chem. Soc. Rev. 1998, 27, 395.
115. Zhang, J.; Flippen-Anderson, J. L.; Kozikowski, A. P. J. Org. Chem. 2001, 66, 7555.
116. For selected routes to 4,4-disubtituted azetidinones, see: (a) Ageno, G.; Banfi, L.; Cascio, G.; Guanti, G.; Manghisi, E.; Riva, R.; Rocca, V. Tetrahedron 1995, 51, 8121.
117. (b) DeKimpe, N.; Tehrani, K. A.; Fonck, G. J. Org. Chem. 1996, 61, 6500.
118. (c) Palomo, C.; Aizpurua, J. M.; Garcia, J. M.; Galarza, R.; Legido, M.; Urchegui, R.; Román, P.; Luque, A.; Server-Carrio, J.; Linden, A. J. Org. Chem. 1997, 62, 2070.
119. (d) Gerona-Navarro, G.; Garcia-López, M. T.; González-Mniz, R. J. Org. Chem. 2002, 67, 3953.
120. (e) Campomanes, P.; Menendez, M. I.; Sordo, T. L. J. Org. Chem. 2003, 68, 6685.
121. For the preparation of quaternary tetrahydroisoquinoline-3-carboxylic acid derivatives, see: (a) Vicario, J. L.; Badia, D.; Carrillo, L.; Etxebarria, J. Curr. Org. Chem. 2003, 7, 1775.
122. (b) Kawabata, T.; Ozturk, O.; Suzuki, H.; Fuji, K. Synthesis 2003, 505.
123. (c) Alezra, V.; Bonin, M.; Micouin, L.; Husson, H. P. Tetrahedron Lett. 2001, 42, 2111.
124. (d) Chinchilla, R.; Galindo, N.; Najera, C. Synthesis 1999, 704.
125. (e) Ma, D.; Ma, Z.; Kozikowski, A. P.; Pshenichkin, S.; Wroblewski, J. T. Bioorg. Med. Chem. Lett. 1998, 8, 2447.
126. (f) Seebach, D.; Dziadulewicz, E.; Behrendt, L.; Cantoreggi, S.; Fitzi, R. Liebigs Ann. Chem. 1989, 1215.
127. (g) Bajgrowicz, J.; El Achquar, A.; Roumestant, M.-L.; Pigière, C.; Viallefont, P. Heterocycles 1986, 24, 2165.
128. (a) Kondo, K.; Sodeoka, M.; Mori, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4219.
129. (b) Kondo, K.; Sodeoka, M.; Mori, M.; Shibasaki, M. Synthesis 1993, 920.
130. (c) Wipf, P.; Kim, Y. J. Am. Chem. Soc. 1994, 116, 11678.
131. (d) Blades, K.; Cockerill, G. S.; Easterfield, H. J.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1615.
132. Banerjee, A. K.; Azocar, J. A.; Vera, W. Synth. Commun. 1999, 29, 2995.
133. (a) Luche, J. L. J. Am. Chem. Soc. 1978, 100, 2226.
134. (b) Abruscato, G. J.; Tidwell, T. T. J. Org. Chem. 1972, 37, 4151.
135. Acetylation of the crude product was necessary in this case to facilitate chromatographic purification.
136. Nakagawa, T. W.; Andrews, L. J.; Reefer, R. M. J. Am. Chem. Soc. 1960, 82, 269.
137. (a) Wipf, P.; Jung, J.-K. Chem. Rev. 1999, 99, 1469.
138. (b) Ohkata, K.; Tamura, Y.; Shetuni, B. B.; Takagi, R.; Miyanaga, W.; Kojima, S.; Paquette, L. A. J. Am. Chem. Soc. 2004, 126, 16783.
139. The calculations were performed with Spartan'04 for Macintosh, Wavefunction Inc., Irvine, CA 92612.
140. Mattingly, P. G.; Miller, M. J. J. Org. Chem. 1980, 45, 410.
141. (a) Chang, C. Y.; Yang, T. K. Tetrahedron: Asymmetry 2003, 14, 2081.
142. (b) Romero, A. G.; Darlington, W. H.; McMillan, M. W. J. Org. Chem. 1997, 62, 6582.
143. Qabar, M. N.; Kahn, M. Tetrahedron Lett 1996, 37, 965.
144. (a) Chiara, J. L.; Destabel, C.; Gallego, P.; Marco-Contelles, J. J. Org. Chem. 1996, 61, 359.
145. (b) Yang, H. W.; Romo, D. J. Org. Chem. 1999, 64, 7657.
146. (c) Keck, G. E.; Wager, T. T.; McHardy, S. F. Tetrahedron 1999, 55, 11755
147. (a) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
148. (b) Blakemore, P. R.; Kim, S.-K.; Schulze, V. K.; White, J. D.; Yokochi, A. F. T. J. Chem. Soc., Perkin Trans. 1 2001, 1831.
149. (c) Chow, C. P.; Shea, K. J.; Sparks, S. M. Org. Lett. 2002, 4, 2637
150. (a) King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089.
151. (b) Malpass, J. R.; Smith, C. Tetrahedron Lett. 1992, 33, 273.
152. (a) Graham, S. L.; Scholz, T. H. Tetrahedron Lett. 1990, 31, 6269.
153. (b) Anderson, J. C.; Flaherty, A.; Swarbrick, M. E. J. Org. Chem. 2000, 65, 9152.
154. Keck, G. E.; McHardy, S. F.; Murry, J. A. Tetrahedron Lett. 1994, 34, 6215
155. Yus, M.; Radivoy, G.; Alonso, F. Synthesis 2001, 914
156. (a) Cardani, S.; Gennari, C.; Scolastico, C.; Villa, R. Tetrahedron 1989, 45, 7397.
157. (b) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
158. (a) Cicchi, S.; Goti, A.; Brandi, A.; Guarna, A.; De Sarlo, F. Tetrahedron Lett. 1990, 31, 3351.
159. (b) Gouverneur, V.; Ghosez, L. Tetrahedron Lett. 1991, 32, 5349.
160. (c) Ritter, A. R.; Miller, M. J. J. Org. Chem. 1994, 59, 4602.
161. (a) Black, D. S. C.; Brown, R. F. C.; Wade, A. M. Aust. J. Chem. 1972, 25, 2155.
162. (b) Black, D. S. C.; Brown, R. F. C.; Wade, A. M. Aust. J. Chem. 1972, 25, 2429.
163. (c) Keck, G. E.; Webb, R. R.; Yates, J. B. Tetrahedron 1981, 37, 4007.
164. (d) Crossley, M. J.; Crumbie, R. L.; Fung, Y. M.; Potter, J. J.; Pegler, M. A. Tetrahedron Lett. 1987, 28, 2883.
165. (e) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Schofield, C. J. J. Chem. Soc., Chem. Commun. 1990, 720.
166. (f) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Schofield, C. J. Tetrahedron 1991, 47, 5835
167. (g) Leeson, P. D.; Williams, B. J.; Rowley, M.; Moore, K. W.; Baker, R.; Kemp, J. A.; Priestley, T.; Foster, A. C.; Donald, A. E. Bioorg. Med. Chem. Lett. 1993, 3, 71.
168. (h) Tiecco, M.; Testaferri, L.; Tingoli, M.; Marini, F. J. Chem. Soc., Chem. Commun. 1994, 221.
169. (i) Thomas, A.; Rajappa, S. Tetrahedron 1995, 51, 10571.
170. (j) Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E.; Morganti, S.; Rizzato, E.; Spinelli, D.; Dell'Erba, C.; Petrillo, G.; Tavani, C. Tetrahedron 2004, 60, 11011.
171. Dong, L.; Miller, M. J. J. Org. Chem. 2002, 67, 4759.
172. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
173. Loudon, G. M.; Radhakrishna, A. S.; Almond, M. R.; Blodgett, J. K.; Boulin, R. H. J. Org. Chem. 1984, 49, 4272.