Radical Cyclization of Haloacetals: The Ueno-Stork Reaction

Xavier J. Salom-Roig; Fabrice Dénès; Philippe Renaud

doi:10.1055/s-2004-831161

REVIEW

Radical Cyclization of Haloacetals: The Ueno-Stork Reaction

Xavier J. Salom-Roig, Fabrice Dénès, Philippe Renaud*
University of Berne, Department of Chemistry and Biochemistry, Freiestrasse 3, 3000 Berne 9, Switzerland
Fax: +41(31)6313426; e-Mail: philippe.renaud@ioc.unibe.ch ;

Abstract

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Abstract

The formation of the C-C bond using radical cyclization of haloacetals (Ueno-Stork reaction) has proven to be an extremely efficient method to access γ-lactones and related compounds. This reaction is also highly attractive for the regio- and stereoselective introduction of side chains to cyclic and acyclic allylic alcohols. It has been used as a key step in many natural product syntheses and has proven to be particularly efficient for the stereoselective generation of quaternary carbon centers. This review focuses on the different methods available to carry out this radical cyclization, as well as on the stereochemical aspect of the reaction and its applications in total synthesis.

1 Introduction
2 Preparation of Haloacetals and Related Compounds
3 Methods for Radical Cyclization
3.1 Radical Chain Reactions
3.1.1 Tin Hydride
3.1.2 Substitute for Tin Hydride
3.1.3 Atom and Group Transfer Reactions
3.1.4 The Fragmentation Method
3.1.5 Cyclization Followed by Formation of a C-X Bond
3.2 Non-Chain Reactions
3.2.1 Reductive Processes
3.2.1.1 Samarium(II) Diiodide
3.2.1.2 Indium
3.2.1.3 Titanium and Zirconium
3.2.1.4 Organomagnesium Reagents
3.2.1.5 Organomanganese Reagents
3.2.1.6 Chromium(II) Species
3.2.1.7 Nickel-Catalyzed Carbozincation
3.2.1.8 Cobalt-Mediated Cyclizations
3.2.1.9 Photoelectron Transfer
3.2.2 Oxidative Processes
4 Stereochemical Considerations
4.1 The Role of the Acetal Center
4.1.1 4-Substituted 2-Alkoxytetrahydrofurans
4.1.2 3,4-Disubstituted 2-Alkoxytetrahydrofurans
4.1.3 4,5-Disubstituted 2-Alkoxytetrahydrofurans
4.1.4 3,4,5-Trisubstituted 2-Alkoxytetrahydrofurans
4.1.5 3-Substituted 2-Alkoxy-4-methylene-tetrahydrofurans
4.1.6 Tetrahydrofurans Derivatives
4.1.7 Control of the Absolute Configuration of the Acetal Center
4.1.8 Regioselectivity Control by the Acetal Center
4.2 The Role of the Allylic Center
4.3 Stereochemistry of the Ring Junction
4.4 Cyclizations Leading to Fused Bicyclic Systems
4.5 Reactions Leading to Spiro Compounds
4.6 Control of the Stereochemistry of Follow-Up Reactions
5 Application in Natural Product Synthesis
5.1 Monocyclic Tetrahydrofurans and γ-Lactones
5.2 Fused Bicyclic Compounds
5.2.1 Use of Cyclic Alkenes
5.2.2 Use of Cyclic Radicals
5.3 Spirocyclic Compounds
5.4 Six-Membered Rings
5.5 Bridged Systems
5.6 Bicyclic Compounds via Transannular Reactions
5.7 Polycyclic Systems via Cascade Cyclizations
5.8 Introduction of Side Chain via an Acetal Tether
5.8.1 Acyclic Compounds
5.8.2 Cyclic Systems
5.8.3 Addition of Two Side Chains at Once: Prostaglandin and Related Syntheses
6 Conclusion

Key words

radicals - cyclizations - acetals - lactones - tethers - total synthesis - stereoselectivity

Full Text

References

1 Curran DP. Synthesis 1988, 417

2 Curran DP. Synthesis 1988, 489

3 Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds Pergamon; Oxford: 1988.

4 Curran DP. Porter NA. Giese B. Stereochemistry of Radical Reactions VCH; Weinheim: 1996.

5 Fossey J. Lefort D. Sorba J. Free Radicals in Organic Synthesis Wiley; Chichester: 1995.

6 Motherwell WB. Crich D. Free Radical Chain Reactions in Organic Synthesis Academic Press; London: 1992.

7 Parsons AF. Bar G. Chem. Soc. Rev. 2003, 32: 251

8 Renaud P. Sibi MP. Radicals in Organic Synthesis Wiley-VCH; Weinheim: 2001.

9 Jasperse CP. Curran DP. Fevig TL. Chem. Rev. 1991, 91: 1237

10 McCarrol AJ. Walton JC. Angew. Chem. Int. Ed. 2001, 40: 2224

11 Giese B. Org. React. 1996, 48: 301

12 Bowman WR. Fletcher AJ. Potts GBS. J. Chem. Soc., Perkin Trans. 1 2002, 2747

13 Fallis AG. Brinza IM. Tetrahedron 1997, 53: 17543

14 Yet L. Tetrahedron 1999, 55: 9349

15 Bowman WR. Cloonan MO. Krintel SL. J. Chem. Soc., Perkin Trans. 1 2001, 2885

16 Zhang W. Tetrahedron 2001, 57: 7237

17 Ishibashi H. Sato T. Ikeda M. Synthesis 2002, 695

18 Rheault TR. Sibi MP. Synthesis 2003, 803

19 Lee E. In Radicals in Organic Synthesis Vol. 2: Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001. p.303

20 Clive DLJ. Beaulieu PL. J. Chem. Soc., Chem. Commun. 1983, 307

21 Hanessian S. Di Fabio R. Marcoux JF. Prud’homme M. J. Org. Chem. 1990, 55: 3436

22 Beckwith ALJ. Pigou PE. J. Chem. Soc., Chem. Commun. 1986, 85

23 Curran DP. Chang C.-T. J. Org. Chem. 1989, 54: 3140

24 Curran DP. Tamine J. J. Org. Chem. 1991, 56: 2746

25 Ueno Y. Chino K. Watanabe M. Moriya O. Okawara M. J. Am. Chem. Soc. 1982, 104: 5564

26 Ueno Y. Moriya O. Chino K. Watanabe M. Okawara M. J. Chem. Soc., Perkin Trans. 1 1986, 1351

27 Stork G. Mook R. Biller SA. Rychnovsky SD. J. Am. Chem. Soc. 1983, 105: 3741

28 Stork G. Bull. Chem. Soc. Jpn. 1988, 61: 149

29 Stork G. Bull. Soc. Chim. Fr. 1990, 675

30 Smith TW. Butler GB. J. Org. Chem. 1978, 43: 6

31 Dräger G. Garming A. Maul C. Noltemeyer M. Thiericke R. Zerlin M. Kirschning A. Chem.-Eur. J. 1998, 4: 1324

32 Grieco PA. Oguri T. Yokoyama Y. Tetrahedron Lett. 1978, 419

33 Stork G. Mook R. J. Am. Chem. Soc. 1983, 105: 3720

34 Stork G. Sher PM. J. Am. Chem. Soc. 1986, 108: 303

35 Petrzilka M. Helv. Chim. Acta 1978, 61: 2286

36 Engman L. Gupta V. J. Org. Chem. 1997, 62: 157

37 Srikrishna A. Nagaraju S. Sharma GVR. Synth. Commun. 1992, 22: 1127

38 Yorimitsu H. Oshima K. In Radicals in Organic Synthesis Vol. 1: Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001. p.11

39 Villar F. Equey O. Kolly-Kovac T. Renaud P. Chem.-Eur. J. 2003, 9: 1566

40 Inoue K. Sawada A. Shibata I. Baba A. Tetrahedron Lett. 2001, 42: 4661

41 Rai R. Collum DB. Tetrahedron Lett. 1994, 35: 6221

42 Stork G. Sher PM. J. Am. Chem. Soc. 1983, 105: 6765

43 Studer A. Amrein S. Synthesis 2002, 835

44 Nakamura T. Yorimitsu H. Shinokubo H. Oshima K. Synlett 1999, 1415

45 Nakamura T. Yorimitsu H. Shinokubo H. Oshima K. Bull. Chem. Soc. Jpn. 2001, 74: 747

46 Chuang C.-P. Jiang VJ. J. Chin. Chem. Soc. 1989, 36: 177

47 Yamazaki O. Yamaguchi K. Yokoyama M. Togo H. J. Org. Chem. 2000, 65: 5440

48 Mikami S. Fujita K. Nakamura T. Yorimitsu H. Shinokubo H. Matsubara S. Oshima K. Org. Lett. 2001, 3: 1853

49 Takami K. Mikami S. Yorimitsu H. Shinokubo H. Oshima K. Tetrahedron 2003, 59: 6627

50 Fujita K. Nakamura T. Yorimitsu H. Oshima K. J. Am. Chem. Soc. 2001, 123: 3137

51 Graham SR. Murphy JA. Coates D. Tetrahedron Lett. 1999, 40: 2415

52 Kita Y. Nambu H. Ramesh NG. Anilkumar G. Matsugi M. Org. Lett. 2001, 3: 1157

53 Nambu H. Anilkumar G. Matsugi M. Kita Y. Tetrahedron 2003, 59: 77

54 Yorimitsu H. Shinokubo H. Oshima K. Chem. Lett. 2000, 104

55 Yorimitsu H. Shinokubo H. Oshima K. Bull. Chem. Soc. Jpn. 2001, 74: 225

56 Roy SC. Guin C. Rana KK. Maiti G. Tetrahedron 2002, 58: 2435

57 Byers J. In Radicals in Organic Synthesis Vol. 1: Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001. p.72

58 Ollivier C. Bark T. Renaud P. Synthesis 2000, 1598

59 Yorimitsu H. Nakamura T. Shinokubo H. Oshima K. Omoto K. Fujimoto H. J. Am. Chem. Soc. 2000, 122: 11041

60 Ichinose Y. Matsunaga S.-i. Fugami K. Oshima K. Utimoto K. Tetrahedron Lett. 1989, 30: 3155

61 Albrecht U. Wartchow R. Hoffmann HMR. Angew. Chem., Int. Ed. Engl. 1992, 31: 910

62 Breithor M. Herden U. Hoffmann HMR. Tetrahedron 1997, 53: 8401

63 Hoffmann HMR. Herden U. Breithor M. Rhode O. Tetrahedron 1997, 53: 8383

64 Rhode O. Hoffmann HMR. Tetrahedron 2000, 56: 6479

65 Luebbers T. Schaefer HJ. Synlett 1991, 861

66 Boivin J. Camara J. Zard SZ. J. Am. Chem. Soc. 1992, 114: 7909

67 Tanaka S. Nakamura T. Yorimitsu H. Shinokubo H. Matsubara S. Oshima K. Synlett 2001, 1278

68 Ferrier RJ. Petersen PM. Taylor MA. J. Chem. Soc., Chem. Commun. 1989, 1247

69 Ferrier RJ. Petersen PM. Tetrahedron 1990, 46: 1

70 Keck GE. Burnett DA. J. Org. Chem. 1987, 52: 2958

71 Kim S. Lim CJ. Song C. Chung W.-j. J. Am. Chem. Soc. 2002, 124: 14306

72 Nakamura E. Inubushi T. Aoki S. Machii D. J. Am. Chem. Soc. 1991, 113: 8980

73 Mayer S. Prandi J. Tetrahedron Lett. 1996, 37: 3117

74 Mayer S. Prandi J. Bamhaoud T. Bakkas S. Guillou O. Tetrahedron 1998, 54: 8753

75 Ollivier C. Renaud P. J. Am. Chem. Soc. 2001, 123: 4717

76 Pandey G. Rao KSSP. Angew. Chem., Int. Ed. Engl. 1995, 34: 2669

77 Pandey G. Rao KSSP. Palit DK. Mittal JP. J. Org. Chem. 1998, 63: 3968

78 Pandey G. Rao KSSP. Rao KVN. J. Org. Chem. 2000, 65: 4309

79 Fukuzawa S.-i. Tsuchimoto T. Synlett 1993, 803

80 Yanada R. Nishimori N. Matsumura A. Fujii N. Takemoto Y. Tetrahedron Lett. 2002, 43: 4585

81 Yanada R. Koh Y. Nishimori N. Matsumura A. Obka S. Mitsuya H. Fujii N. Takemoto Y. J. Org. Chem. 2004, 69: 2417

82 Zhou L. Hirao T. J. Org. Chem. 2003, 68: 1633

83 Fujita K. Yorimitsu H. Oshima K. Synlett 2002, 337

84 Hayashi Y. Shinokubo H. Oshima K. Tetrahedron Lett. 1998, 39: 63

85 Inoue A. Shinokubo H. Oshima K. Org. Lett. 2000, 2: 651

86 Inoue R. Nakao J. Shinokubo H. Oshima K. Bull. Chem. Soc. Jpn. 1997, 71: 2039

87 Tang J. Shinokubo H. Oshima K. Synlett 1998, 1075

88 Tang J. Shinokubo H. Oshima K. Tetrahedron 1999, 55: 1893

89 Giese B. Thoma G. Helv. Chim. Acta 1991, 74: 1135

90 Lübbers T. Schäfer HJ. Synlett 1990, 44

91 Lübbers T. Schäfer HJ. Synlett 1992, 743

92 Hackmann C. Schäfer HJ. Tetrahedron 1993, 49: 4559

93 Vaupel A. Knochel P. Tetrahedron Lett. 1994, 35: 8349

94 Vaupel A. Knochel P. Tetrahedron Lett. 1995, 36: 231

95 Vaupel A. Knochel P. J. Org. Chem. 1996, 61: 5743

96 Plietker B. Metz P. Tetrahedron Lett. 1998, 39: 7827

97 Plietker B. Seng D. Fröhlich R. Metz P. Eur. J. Org. Chem. 2002, 3669

98 Riguet E. Klement I. Reddy CK. Cahiez G. Knochel P. Tetrahedron Lett. 1996, 37: 5865

99 Banerjee R. Chem. Rev. 2003, 103: 2083

100 Begley MJ. Bhandal H. Hutchinson JH. Pattenden G. Tetrahedron Lett. 1987, 28: 1317

101 Busato S. Tinembart O. Zhang Z.-d. Scheffold R. Tetrahedron 1990, 46: 3155

102 Lee ER. Lakomy I. Bigler P. Scheffold R. Helv. Chim. Acta 1991, 74: 146

103 Pattenden G. Chem. Soc. Rev. 1988, 17: 361

104 Iqbal J. Bhatia B. Nayyar NK. Chem. Rev. 1994, 94: 519

105 Tada M. J. Synth. Org. Chem. Jpn. 1998, 56: 544

106 Torii S. Inokuchi T. Yukawa T. J. Org. Chem. 1985, 50: 5875

107 Ali A. Harrowven DC. Pattenden G. Tetrahedron Lett. 1992, 33: 2851

108 Last K. Hoffmann HMR. Synthesis 1989, 901

109 Giese B. Erdmann P. Göbel T. Springer R. Tetrahedron Lett. 1992, 33: 4545

110 Ladlow M. Pattenden G. Tetrahedron Lett. 1984, 25: 4317

111 Baldwin JE. Moloney MG. Parsons AF. Tetrahedron 1991, 47: 155

112 Bhandal H. Pattenden G. Russell JJ. Tetrahedron Lett. 1986, 27: 2299

113 Bhandal H. Patel VF. Pattenden G. Russell JJ. J. Chem. Soc., Perkin Trans. 1 1990, 2691

114 Bambaoud T. Prandi J. Chem. Commun. 1996, 1229

115 Fujioka T. Nakamura T. Yorimitsu H. Oshima K. Org. Lett. 2002, 4: 2257

116 Ikeda Y. Nakamura T. Yorimitsu H. Oshima K. J. Am. Chem. Soc. 2002, 124: 6514

117 Wakabayashi K. Yorimitsu H. Oshima K. J. Am. Chem. Soc. 2001, 123: 5374

118 Tsuji T. Yorimitsu H. Oshima K. Angew. Chem. Int. Ed. 2002, 41: 4137

119 Palacios SM. Rossi RA. J. Phys. Org. Chem. 1990, 3: 812

120 Nazareno MA. Palacios SM. Rossi RA. J. Phys. Org. Chem. 1993, 6: 421

121 Cossy J. Ranaivosata J.-L. Bellosta V. Tetrahedron Lett. 1994, 35: 8161

122 Weiguny J. Schäfer HJ. Liebigs Ann. Chem. 1994, 235

123 Panico R. Powell WH. Richer J.-C. A Guide to IUPAC Nomenclature of Organic Compounds Recommendation 1993 Blackwell; Oxford: 1993.

124 López JC. Fraser-Reid B. Chem. Commun. 1997, 2251

125 López JC. Gómez AM. Fraser-Reid B. J. Chem. Soc., Chem. Commun. 1994, 1533

126 López JC. Gómez AM. Fraser-Reid B. Aust. J. Chem. 1995, 48: 333

127 McCague R. Pritchard RG. Stoodley RJ. Williamson DS. Chem. Commun. 1998, 2691

128 Beckwith ALJ. Page DM. J. Org. Chem. 1998, 63: 5144

129 Beckwith ALJ. Schiesser CH. Tetrahedron 1985, 41: 3925

130 Beckwith ALJ. Zimmermann J. J. Org. Chem. 1991, 56: 5791

131 Spellmeyer DC. Houk KN. J. Org. Chem. 1987, 52: 959

132 Corminboeuf O. Renaud P. Schiesser CH. Chem.-Eur. J. 2003, 9: 1578

133 Villar F. Renaud P. Tetrahedron Lett. 1998, 39: 8655

134 Nouguier R. Gastaldi S. Stien D. Bertrand M. Villar F. Andrey O. Renaud P. Tetrahedron: Asymmetry 2003, 14: 3005

135 Renaud P. Beaufils F. Feray L. Schenk K. Angew. Chem. Int. Ed. 2003, 42: 4230

136 Idris MS. Larsen DS. Pritchard RG. Schofield A. Stoodley RJ. Tiffin PD. J. Chem. Soc., Perkin Trans. 1 2000, 2195

137 Hoffmann RW. Chem. Rev. 1989, 89: 1841

138 Giese B. Damm W. Batra R. Chemtracts: Org. Chem. 1994, 7: 355

139 Kahn M. Chen B. Tetrahedron Lett. 1987, 28: 1623

140 Stork G. Mah R. Tetrahedron Lett. 1989, 30: 3609

141 Stork G. Kahn M. J. Am. Chem. Soc. 1985, 107: 500

142 Beckwith ALJ. Page DM. Tetrahedron 1999, 55: 3245

143 Haudrechy A. Sinaӱ P. Carbohydr. Res. 1991, 216: 375

144 Dalla V. Pale P. Tetrahedron Lett. 1992, 33: 7857

145 López JC. Gómez AM. Fraser-Reid B. J. Org. Chem. 1995, 60: 3871

146 Renaud P. In Radicals in Organic Synthesis Vol. 1: Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001.

147 Yokomatsu T. Shimizu T. Yuasa Y. Shibuya S. Synlett 1995, 1280

148 Lau WY. Zhang L. Wang J. Cheng D. Zhao K. Tetrahedron Lett. 1996, 37: 4297

149 Lavallée J.-F. Just G. Tetrahedron Lett. 1991, 32: 3469

150 Yoo S.-E. Im M.-NK. Cho I. Bull. Korean Chem. Soc. 1994, 15: 680

151 Srikrishna A. Danieldoss S. Venkateswarlu S. Sattigeri JA. J. Indian Chem. Soc. 1997, 74: 864

152 Srikrishna A. Danieldoss S. Synth. Commun. 2001, 31: 2357

153 Morikawa T. Nishiwaki T. Iitaka Y. Kobayashi Y. Tetrahedron Lett. 1987, 28: 671

154 Itoh T. Sakabe K. Kudo K. Ohara H. Takagi Y. Kihara H. Zagatti P. Renou M. J. Org. Chem. 1999, 64: 252

155 Morikawa T. Nishiwaki T. Kobayashi Y. Tetrahedron Lett. 1989, 30: 2407

156 Yadav JS. Gadgil VR. J. Chem. Soc., Chem. Commun. 1989, 1824

157 Itoh T. Sakabe K. Kudo K. Zagatti P. Renou M. Tetrahedron Lett. 1998, 39: 4071

158 Itoh T. Kudo K. Tanaka N. Zagatti P. Renou M. Enantiomer 2001, 6: 43

159 Villar F. Equey O. Renaud P. Org. Lett. 2000, 2: 1061

160 Moriya O. Okawara M. Ueno Y. Chem. Lett. 1984, 1437

161 López JC. Fraser-Reid B. J. Am. Chem. Soc. 1989, 111: 3450

162 Chapleur Y. Moufid N. J. Chem. Soc., Chem. Commun. 1989, 39

163 Moufid N. Chapleur Y. Mayon P. J. Chem. Soc., Perkin Trans. 1 1992, 991

164 Tulshian D. Czarniecki M. Doll RJ. Ahn HS. J. Med. Chem. 1993, 36: 1210

165 Begley MJ. Ladlow M. Pattenden G. J. Chem. Soc., Perkin Trans. 1 1988, 1095

166 Dulcère J.-P. Mihoubi MN. Rodriguez J. J. Org. Chem. 1993, 58: 5709

167 White JD. Shin H. Tetrahedron Lett. 1997, 38: 1141

168 Armer RE. Dutton CJ. Fenner BR. Greenwood SDW. Hall KT. Rutge AJ. Bioorg. Med. Chem. Lett. 1998, 8: 139

169 Shimizu M. Kamikubo T. Ogasawara K. Synlett 1998, 655

170 McDonald CE. Dugger RW. Tetrahedron Lett. 1988, 29: 2413

171 Wee AGH. Tetrahedron 1990, 46: 5065

172 Metz P. Stölting J. Läge M. Krebs B. Angew. Chem., Int. Ed. Engl. 1994, 33: 2195

173 Srikrishna A. Viswajanani R. Sattigeri JA. J. Chem. Soc., Chem. Commun. 1995, 469

174 Holton RA. Juo RR. Kim HB. Williams AD. Harusawa S. Lowenthal RE. Yogai S. J. Am. Chem. Soc. 1988, 110: 6558

175 Pezechk M. Brunetiere AP. Lallemand JY. Tetrahedron Lett. 1986, 27: 3715

176 Venugopalan B. Karnik PJ. Bapat CP. Chatterjee DK. Iyer N. Lepcha D. Eur. J. Med. Chem. 1995, 30: 697

177 Ami Ei. Rajesh S. Wang J. Kimura T. Hayashi Y. Kiso Y. Ishida T. Tetrahedron Lett. 2002, 43: 2931

178 Srikrishna A. Krishnan K. Tetrahedron Lett. 1988, 29: 4995

179 Audin C. Lancelin J.-M. Beau J.-M. Tetrahedron Lett. 1988, 29: 3691

180 De Mesmaeker A. Hoffmann P. Ernst B. Tetrahedron Lett. 1989, 30: 57

181 Venugopalan B. Shinde SL. Karnik PJ. Tetrahedron Lett. 1993, 34: 6305

182 Venugopalan B. Karnik PJ. Shinde S. J. Chem. Soc., Perkin Trans. 1 1996, 1015

183 Graham SR. Murphy JA. Kennedy AR. J. Chem. Soc., Perkin Trans. 1 1999, 3071

184 Sharma GVM. Chander AS. Reddy VG. Krishnudu K. Rao MHVR. Kunwar AC. Tetrahedron Lett. 2000, 41: 1997

185 Kim KS. Kim JH. Kim YK. Park YS. Hahn CS. Carbohydr. Res. 1989, 194: C1

186 Srikrishna A. Sharma GVR. Nagaraju S. Synth. Commun. 1992, 22: 1221

187 Harrison T. Pattenden G. Meyers PL. Tetrahedron Lett. 1988, 29: 3869

188 Harrison T. Myers PL. Pattenden G. Tetrahedron 1989, 45: 5247

189 Srikrishna A. Nagaraju S. Venkateswarlu S. Tetrahedron Lett. 1994, 35: 429

190 Clive DLJ. Huang X. Tetrahedron 2001, 57: 3845

191 Labadie GR. Cravero RM. Gonzalez-Sierra M. Tetrahedron Lett. 2001, 42: 1811

192 Zanoni G. Re S. Meriggi A. Castronovo F. Vidari G. Tetrahedron: Asymmetry 2001, 12: 1785

193 Katsumata A. Takasu K. Ihara M. Heterocycles 1999, 51: 733

194 Hatakeyama S. Ochi N. Numata H. Takano S. J. Chem. Soc., Chem. Commun. 1988, 1202

195 Kim M. Kawada K. Gross RS. Watt DS. J. Org. Chem. 1990, 55: 504

196 Ihara M. Taniguchi N. Fukumoto K. Kametani T. J. Chem. Soc., Chem. Commun. 1987, 1438

197 Ihara M. Yasui K. Taniguchi N. Fukumoto K. J. Chem. Soc., Perkin Trans. 1 1990, 1469

198 White JD. Blakemore PR. Green NJ. Hauaser EB. Hoéoboski MA. Keown LE. Kolz CSN. Phillips BW. J. Org. Chem. 2002, 67: 7750

199 Hindson AC. MacCorquodale F. Walton JC. J. Chem. Soc., Perkin Trans. 2 1993, 871

200 Vite GD. Alonso R. Fraser-Reid B. J. Org. Chem. 1989, 54: 2268

201 Alonso RA. Vite GD. McDevitt RE. Fraser-Reid B. J. Org. Chem. 1992, 57: 573

202 Henry KJ. Fraser-Reid B. J. Org. Chem. 1994, 59: 5128

203 Nagano H. Tada A. Isobe Y. Yajima T. Synlett 2000, 1193

204 Parsons PJ. Penkett CS. Shell AJ. Chem. Rev. 1996, 96: 195

205 Malacria M. Chem. Rev. 1996, 96: 289

206 Yadav JS. Gadgil VR. J. Chem. Soc., Chem. Commun. 1989, 1824

207 Yadav JS. Praveen TKK. Gadgil VR. Tetrahedron Lett. 1992, 33: 3687

208 Nagano H. Ohtani Y. Odake E. Nakagawa J. Mori Y. Yajima T. J. Chem. Res., Synop. 1999, 338

209 Labadie GR. Cravero RM. Gonzalez-Sierra M. Tetrahedron Lett. 2001, 42: 1811

210 Kim S. Hyun OhD. Synlett 1998, 525

211 Lee E. Lim JW. Yoon CH. Sung Y.-s. Kim YK. J. Am. Chem. Soc. 1997, 119: 8391

212 Woltering TJ. Hoffmann HMR. Tetrahedron 1995, 51: 7389

213 Stork G. Franklin PJ. Aust. J. Chem. 1992, 45: 275

214 Nakai E.-i. Kitahara E.-i. Sayo N. Ueno Y. Nakai T. Chem. Lett. 1985, 1725

215 Rao AVR. Gurjar MK. Bose DS. Devi RR. J. Org. Chem. 1991, 56: 1320

216 Rao AVR. Bhanu MN. Sharma GVM. Tetrahedron Lett. 1993, 34: 707

217 Yadav JS. Praveen Kumar TK. Maniyan PP. Tetrahedron Lett. 1993, 34: 2965

218 Hareau-Vittini G. Kocienski P. Reid G. Synthesis 1995, 1007

219 Miyaoka H. Nagaoka H. Okamura T. Yamada Y. Chem. Pharm. Bull. 1989, 37: 2882

220 Hashimoto K. Shirahama H. Tetrahedron Lett. 1991, 32: 2625

221 Montchamp J.-L. Peng J. Frost JW. J. Org. Chem. 1994, 59: 6999

222 Gössinger E. Schwartz A. Sereinig N. Tetrahedron 2001, 57: 3045

223 Stork G. La Clair JJ. Spargo P. Nargund RP. Totah N. J. Am. Chem. Soc. 1996, 118: 5304

224 Hutchinson JH. Pattenden G. Myers PL. Tetrahedron Lett. 1987, 28: 1313

225 Begley MJ. Cheshire DR. Harrison T. Hutchinson JH. Myers PL. Pattenden G. Tetrahedron 1989, 45: 5215

226 Yamane T. Izhizaki M. Suzuki M. Takahashi M. Hiroya K. Takano S. Ogasawara K. Heterocycles 1996, 42: 65

227 Yamada O. Ogasawara K. Org. Lett. 2000, 2: 2785

228 Yamada O. Ogasawara K. Tetrahedron Lett. 1998, 39: 7747

229 Tsukuda T. Watanabe M. Ontsuka H. Hattori K. Shirai M. Bioorg. Med. Chem. Lett. 1998, 8: 1825

230 Srikrishna A. Kumar PP. Reddy TJ. Tetrahedron Lett. 1998, 39: 5815

231 Clive DLJ. Yu M. Chem. Commun. 2002, 2380

232 Clive DLJ. Huang X. Tetrahedron 2002, 58: 10243

233 Nicolaou KC. Follmann M. Roecker AJ. Hunt KW. Angew. Chem. Int. Ed. 2002, 41: 2103

234 Yoshimitsu T. Yanagisawa S. Nagaoka H. Org. Lett. 2000, 2: 3751

235 Njardarson JT. McDonald IM. Spiegel DA. Inoue M. Wood JL. Org. Lett. 2001, 3: 2435

236 Matsushita T. Ashida H. Kimachi T. Takemoto Y. Chem. Commun. 2002, 814

237 Stork G. Sher PM. Chen H.-L. J. Am. Chem. Soc. 1986, 108: 6384

238 Larock RC. Lee NH. J. Am. Chem. Soc. 1991, 113: 7815

239 Quan LG. Cha JK. J. Am. Chem. Soc. 2002, 124: 12424