Saturated oxygen heterocycles

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 9, 2000, Pages 1291-1318

  Elliott, Mark C ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; ETHERS; MESOPOROUS MATERIALS; OXYGEN; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

LIGANDS;

AROMATIC COMPOUNDS;

EID: 0034616466     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903885j     Document Type: Review

References (336)

1. Previous reviews: M. C. Elliott, J. Chem. Soc., Perkin Trans, 1, 1998, 4175;
2. M. C. Elliott, Contemp. Org. Synth., 1997, 4, 238;
3. C. J. Burns and D. S. Middleton, Contemp. Org. Synth., 1996, 229;
4. M. C. Elliott, Contemp. Org. Synth., 1994, 1, 457.
5. Y. N. Ito and T. Katsuki, Tetrahedron Lett., 1998, 39, 4325.
6. C. Linde, B. Akermark, P.-O. Norrby and M. Svensson, J. Am. Chem. Soc., 1999, 121, 5083.
7. K. Miura and T. Katsuki, Synlett, 1999, 783.
8. K. M. Ryan, C. Bousquet and D. G. Gilheany, Tetrahedron Lett., 1999, 40, 3613.
9. A. M. Daly, C. T. Dalton, M. F. Renehan and D. G. Gilheany, Tetrahedron Lett., 1999, 40, 3617.
10. M. E. Furrow, S. E. Schaus and E. N. Jacobsen, J. Org. Chem., 1998, 63, 6776;
11. D. A. Annis, J. Am. Chem. Soc., 1999, 121, 4147;
12. J. M. Ready and E. N. Jacobsen, J. Am. Chem. Soc., 1999, 121, 6086.
13. M. K. Gurjar, B. V. N. B. S. Sarma, K. Sadalapure and S. Adhikari, Synthesis, 1998, 1424.
14. R. G. Konsler, J. Karl and E. N. Jacobsen, J. Am. Chem. Soc., 1998, 120, 10780.
15. Q. Yu, Y. Wu, L.-J. Xia, M.-H. Tang and Y.-L. Wu, Chem. Commun., 1999, 129.
16. P. S. Savle, M. J. Lamoreaux, J. F. Berry and R. D. Gandour, Tetrahedron: Asymmetry, 1998, 9, 1843.
17. P. Moussou, A. Archelas, J. Baratti and R: Furstoss, Tetrahedron: Asymmetry, 1998, 9, 1539;
18. M. Cleij, A. Archelas and R. Furstoss, Tetrahedron: Asymmetry, 1998, 9, 1839.
19. A. Scheurer, P. Mosset, M. Spiegel and R. W. Saalfrank, Tetrahedron, 1999, 55, 1063.
20. D. E. De Vos, B. F. Sels, M. Reynaers, Y. V. Subba Rao and P. A. Jacobs, Tetrahedron Lett., 1998, 39, 3221.
21. P. Pietikäinen, Tetrahedron, 1998, 54, 4319.
22. P. Pietikäinen, Tetrahedron Lett., 1999, 40, 1001.
23. A. Lévai, W. Adam, R. T. Fell, R. Gessner, T. Patonay, A. Simon and G. Tóth, Tetrahedron, 1998, 54, 13105.
24. J. P. Collman, Z. Wane, A. Straumanis and M. Quelquejeu, J. Am. Chem. Soc, 1999, 121, 460.
25. R. Zhane, W.-Y. Yu, T.-S. Lai and C.-M. Che, Chem. Commun., 1999, 409.
26. J. H. Espenson, Chem. Commun., 1999, 479.
27. M. C. A. van Vliet, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 1999, 821.
28. W.-D. Wang and J. H. Espenson, J. Am. Chem. Soc., 1998, 120, 11335.
29. H. Adolfsson, A. Converse and K. B. Sharpless, Tetrahedron Lett., 1999, 40, 3991.
30. W. Adam, C. M. Mitchell and C. R. Saha-Möller, Eur. J. Org. Chem., 1999, 785.
31. P. Gisdakis, S. Antonczak, S. Köstlmeier, W. A. Herrmann and N. Rösch, Angeu: Chem., Int. Ed, 1998, 37, 2211.
32. M. Dusi, C. A. Müller, T. Mallat and A. Baiker, Chem. Commun., 1999, 197.
33. C.-J. Liu, W.-Y. Yu, S.-G. Li and C.-M. Che, J. Org. Chem., 1998, 63, 7364.
34. D. R. Pesiri, D. K. Morita, W. Glaze and W. Tumas, Chem. Commun., 1998, 1015.
35. G. R. Haas and J. W. Kolis, Tetrahedron Lett., 1998, 39, 5923.
36. S. Amano, N. Ogawa, M. Ohtsuka, S. Ogawa and N. Chida, Chem. Commun., 1998, 1263;
37. S. Amano, N. Ogawa, M. Ohtsuka and N. Chida, Tetrahedron, 1999, 55, 2205.
38. M. K. Lindvall and A. M. P. Koskinen, J. Org. Chem., 1999, 64, 4596.
39. J. K. Karjalainen, O. E. O. Hormi and D. C. Sherrington, Tetrahedron: Asymmetry, 1998, 9, 1563;
40. J. K. Karjalainen, O. E. O. Hormi and D. C. Sherrington, Tetrahedron: Asymmetry, 1998, 9, 2019;
41. J. K. Karjalainen, O. E. O. Hormi and D. C. Sherrington, Tetrahedron: Asymmetry, 1998, 9, 3895.
42. N. Murase, Y. Hoshino, M. Oishi and H. Yamamoto, J. Org. Chem., 1999, 64, 338.
43. M. B. Francis and E. N. Jacobsen, Angew. Chem., Int. Ed., 1999, 38, 937.
44. M. C. A. van Vliet, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 1999, 263.
45. T. Iwahama, S. Sakaguchi and Y. Ishii, Chem. Commun., 1999, 727.
46. B. Betzemeier, F. Lhermitte and P. Knochel, Synlett, 1999, 489.
47. G. Pozzi, F. Cinato, F. Montanari and S. Quici, Chem. Commun., 1998, 877.
48. C. M. Marson and R. C. Melling, Chem. Commun., 1998, 1223.
49. K. S. Ravikumar, F. Barbier, J.-P. Bégué and D. Bonnet-Delphon, Tetrahedron, 1998, 54, 7457.
50. I. Fernández, J. R. Pedro, A. L. Roselló, R. Ruiz, X. Ottenwaelder and Y. Journaux, Tetrahedron Lett., 1998, 39, 2869.
51. For a general overview of asymmetric catalysis using synthetic polymers, see L. Pu, Tetrahedron: Asymmetry, 1998, 9, 1457.
52. M. W. Cappi, W.-P. Chen, R. W. Flood, Y.-W. Liao, S. M. Roberts, J. Skidmore, J. A. Smith and N. M. Williamson, Chem. Commun., 1998, 1159.
53. P. A. Bentley, M. W. Cappi, R. W. Flood, S. M. Roberts and J. A. Smith, Tetrahedron Lett., 1998, 39, 9297.
54. For the use of poly-Lleucine adsorbed onto silica, see T. Geller and S. M. Roberts, J. Chem. Soc., Perkin Trans, 1, 1999, 1397.
55. W.-P. Chen and S. M. Roberts, J. Chem. Soc., Perkin Trans, 1, 1999, 103.
56. W.-P. Chen, A. L. Egar, M. B. Hursthouse, K. M. A. Malik, J. E. Matthews and S. M. Roberts, Tetrahedron Lett., 1998, 39, 8495.
57. For a full account of this work, see B. Lygo and P. G. Wainwright, Tetrahedron, 1999, 55, 6289.
58. S. Arai, H. Tsuge and T. Shioiri, Tetrahedron Lett., 1998, 39, 7563.
59. S. Aràai, M. Oku, M. Miura and T. Shioiri, Synlett, 1998, 1201.
60. S. Arai and T. Shioiri, Tetrahedron Lett., 1998, 39, 2145;
61. S. Arai, T. Ishida and T. Shioiri, Tetrahedron Lett., 1998, 39, 8299;
62. S. Arai, Y. Shirai, T. Ishida and T. Shioiri, Tetrahedron, 1999, 55, 6375.
63. T. Genski, G. MacDonald, X. Wei, N. Lewis and R. J. K. Taylor, Synlett, 1999, 795.
64. P. Wipf and J.-K. Jung, J. Org. Chem, 1999, 64, 1092.
65. A. D. Briggs, R. F. W. Jackson and P. A. Brown, J. Chem. Soc., Perkin Trans, 1, 1998, 4097.
66. R. Fernández de la Pradilla, S. Castro, P. Manzano, M. MartinOrtega, J. Priego, A. Viso, A. Rodriguez and I. Fonseca, J. Org. Chem., 1998, 63, 4954.
67. P. C. Ray and S. M. Roberts, Tetrahedron Lett., 1999, 40, 1779.
68. B. M. Choudary, M. L. Kantam, B. Bharathi and C. V. Reddy, Synlett, 1998, 1203.
69. K. Yamaguchi, K. Ebitani and K. Kaneda, J. Org. Chem., 1999, 64, 2966.
70. S. Watanabe, Y. Kobayashi, T. Arai, H. Sasai, M. Bougauchi and M. Shibasaki, Tetrahedron Lett., 1998, 39, 7353.
71. K. Daikai, M. Kamaura and J. Inanaga, Tetrahedron Lett., 1998, 39, 7321.
72. S. Watanabe, T. Arai, H. Sasai, M. Bougauchi and M. Shibasaki, J. Org. Chem., 1998, 63, 8090.
73. S. Hu and L. P. Hager, Tetrahedron Lett., 1999, 40, 1641.
74. S. E. Denmark and Z. Wu, Synlett, 1999, 847.
75. Y. Tu, Z.-X. Wang, M. Frohn, M. He, H. Yu, Y. Tang and Y. Shi, J. Org. Chem., 1998, 63, 8475.
76. Z.-X. Wang and Y. Shi, J. Org. Chem., 1998, 63, 3099; M. Frohn, Z.-X. Wang and Y. Shi, J. Org. Chem., 1998, 63, 6425.
77. G.-A. Cao, Z.-X. Wang, Y. Tu and Y. Shi, Tetrahedron Lett., 1998, 39, 4425.
78. Y. Zhu, Y. Tu, H. Yu and Y. Shi, Tetrahedron Lett., 1998, 39, 7819.
79. M. Frohn; M. Dalkiewicz, Y. Tu, Z.-X. Wang and Y. Shi, Tetrahedron Lett., 1998, 63, 2948.
80. D. Yang, M.-K. Wong, Y.-C. Yip, X.-C. Wang, M.-W. Tang, J.-H. Zheng and K.-K. Cheung, J. Am. Chem. Soc., 1998, 120, 5943.
81. D. Yang, Y.-C. Yip, J. Chen and K.-K. Cheung, J. Am. Chem. Soc., 1998, 120, 7659.
82. S. E. Denmark and Z. Wu, J. Org. Chem., 1998, 63, 2811.
83. D. Yang, Y.-C. Yip, G.-S. Jiao and M.-K. Wong, J. Org. Chem., 1998, 63, 8952;
84. D. Yang, G.-S. Jiao, Y.-C. Yip and M.-K. Wong, J. Org. Chem., 1999, 64, 1635.
85. R. W. Murray, M. Singh and N. G. Rath, Tetrahedron Lett., 1998, 39, 2899;
86. R. W. Murray, M. Singh and N. G. Rath, Tetrahedron, 1999, 55, 4539.
87. J. Liu, K. N. Houk, A. Dinoi, C. Fusco and R. Curci, J. Org. Chem:, 1998, 63, 8565.
88. M. Freccero, R. Gandolfi, M. Sarzi-Amadè and A. Rastelli, Tetrahedron, 1998, 54, 6123.
89. R. D. Back, M. N. Glukhovtsev and C. Gonzalez, J. Am. Chem. Soc., 1998, 120, 9902.
90. P. C. B. Page, G. A. Rassias, D. Bethell and M. B. Schilling, J. Org. Chem., 1998, 63, 2774.
91. L. Bohé, M. Lusinchi and X. Lusinchi, Tetrahedron, 1999, 55, 141.
92. A. Armstrong, G. Ahmed, I. Garnett, K. Goacolou and J. S. Wailes, Tetrahedron, 1999, 55, 2341.
93. A. Armstrong and A. G. Draflan, Synlett, 1998, 646;
94. A. Armstrong and A: G. Draffan, Tetrahedron Lett., 1999, 40, 4453.
95. K. Maruyama, M. Ueda.'S. Sasaki, Y. Iwata, M. Miyazawa and M. Miyashita, Tetrahedron Lett., 1998, 39, 4517.
96. For a related report, see: A. J. Jensen and K. Luthman, Tetrahedron Lett., 1998, 39, 3213.
97. W. Adam, H.-G. Degen and C. R. Saha-Möller, J Org. Chem., 1999, 64, 1274.
98. A. N. Nikitenko, B. M. Arshava, I. G. Taran, I. E. Mikerin, V. I. Shvets, Y. E. Raifeld, S. A. Lang, Jr. and V. J. Lee, Tetrahedron, 1998, 54, 11731.
99. W. Adam, M. N. Korb and C. R. Saha-Möller, Eur. J. Org. Chem., 1998, 907;
100. W. Adam, V. R. Stegmann and C. R. Saha-Möller, J. Am. Chem. Soc., 1999, 121, 1879.
101. For the use of ammonium ions as stereodirecting groups in dioxirane epoxidations, see G. Asensio, C. Boix-Bernardini, C. Andreu, M. E. Gonzalez-Nunez, R. Mello, J. O. Edwards and G. B. Carpenter, J. Org. Chem., 1999, 64, 4705.
102. S. E. de Sousa, A. Kee, P. O'Brien and S. T. Watson, Tetrahedron Lett., 1999, 40, 387.
103. S. E. de Sousa, P. O'Brien, C. D. Pilgram, D. Roder and T. D. Towers, Tetrahedron Lett., 1999, 40, 391.
104. W. C. Frank, Tetrahedron: Asymmetry, 1998, 9, 3745.
105. G. Majetich, R. Hick, G.-R. Sun and P. McGill, J. Org. Chem., 1998, 63, 2564.
106. M. W. Rowbottom, N. Mathews and T. Gallagher, J. Chem. Soc., Perkin Trans, 1, 1998, 3927.
107. V. K. Aggarwal, J. G. Ford, S. Fonquerna, H. Adams, R. V. H. Jones and R. Fieldhouse, J. Am. Chem. Soc., 1998, 120, 8328.
108. For another account of this work, see V. K. Aggarwal, Synlett, 1998, 329.
109. For new sulfides in this process, see V. K. Agganval, J. G. Ford, R. V. H. Jones and R. Fieldhouse, Tetrahedron: Asymmetry, 1998, 9, 1801.
110. For application of this method to the synthesis of glycidic amides, see V. K. Aggarwal, P. Blackburn, R. Fieldhouse and R. V. H. Jones, Tetrahedron Lett., 1998, 39, 8517.
111. For another preparation of glycidic amides using sulfur ylides, see F. J. López-Herrera, F. Sarabia-Garcia, G. M. Pedraza-Cebrian and M. S. Pino-González, Tetrahedron Lett., 1999, 40, 1379.
112. V. K. Aggarwal, L. Bell, M. P. Coogan and P. Jubault, Chem. Soc., Perkin Trans, 1, 1998, 2037.
113. C. P. Baird and P. C. Taylor, J. Chem. Soc., Perkin Trans, 1, 1998, 3399.
114. K. Julienne and P. Metzner, J. Org. Chem., 1998, 63, 4532;
115. K. Julienne, P. Metzner and V. Henryon, J. Chem. Soc., Perkin Trans. 1, 1999, 731.
116. Y.-G. Zhou, X.-L: Hou, L.-X. Dai, L.-J. Xia and M.-H. Tang, J. Chem. Soc., Perkin Trans, 1, 1999, 77.
117. For a review see B. Iorga, F. Eymery and P. Savignac, Synthesis, 1999, 207.
118. C. Cramay, R. Ferdinande, M. Degueil-Castaing and B. Maillard, Chem. Commun., 1998, 1855.
119. S. Hu, S. Jayaraman and A. C. Oehlschlager, Tetrahedron Lett., 1998, 39, 8059.
120. S. Hu, S. Jayaraman and A. C. Oehlschlager, J. Org. Chem., 1999, 64, 3719.
121. C. Hertweck and W. Boland, J. Org. Chem., 1999, 64, 4426.
122. For related work, see C. Hertweck and W. Boland, Eur. J. Org. Chem., 1998, 2143.
123. F. Chemla, N. Bernard and J. F. Normant, Tetrahedron Lett., 1999, 40, 75.
124. J. A. Marshall, J. A. Jablonowski and H. Jiang, J. Org. Chem., 1999, 64, 2152.
125. Z.-B. Zhang, Z.-M. Wang, Y.-X. Wang, H.-Q. Liu, G.-X. Lei and M. Shi, Tetrahedron: Asymmetry, 1999, 10, 837.
126. L. He, H.-S. Byun and R. Bittman, Tetrahedron Lett., 1998, 39, 2071.
127. S. Sengupta, D. S. Sarma and D. Das, Tetrahedron: Asymmetry, 1999, 10, 1653.
128. J. M. Concellón, P. L. Bernad, R. Alvarez, A. Rodriguez and B. Baragaña, Tetrahedron Lett., 1999, 40, 2863.
129. C. Agami, F. Couty, H. Mathieu and C. Pilot, Tetrahedron Lett., 1999, 40, 4539.
130. T. Harada, T. Nakamura, M. Kinugasa and A. Oku, Tetrahedron Lett., 1999, 40, 503.
131. J. E. Oliver and W. F. Schmidt, Tetrahedron: Asymmetry, 1998, 9, 1723.
132. S.-K. Kang, T. Yamaguchi, S.-J. Pyun, Y.-T. Lee and T.-G. Baik, Tetrahedron Lett., 1998, 39, 2127.
133. R. S. Coleman and J. D. McKinley, Tetrahedron Lett., 1998, 39, 3433.
134. T. Bach, Synthesis, 1998, 683.
135. T. Bach, J. Schröder, T. Brandi, J. Hecht and K. Harms, Tetrahedron, 1998, 54, 4507.
136. T. Bach and J. Schröder, J. Org. Chem., 1999, 64, 1265.
137. T. Bach and H. Brummerhop, Angew. Chem., Int. Ed., 1998, 37, 3400.
138. L. A. Paquette, T.-L. Shih, Q. Zeng and J. E. Hofierberth, Tetrahedron Lett., 1999, 40, 3519.
139. E. Pinard, M. Gaudry, F. Hénot and A. Thellend, Tetrahedron Lett., 1998, 39, 2739.
140. W.-M. Dai and M. Y. H. Lee, Tetrahedron Lett., 1998, 39, 8149.
141. L . E. Overman and A. L. Tomasi, J. Am. Chem. Soc., 1998, 120, 4039.
142. K. M. Kim, D. J. Jeon and E. K. Ryu, Synthesis, 1998, 835.
143. P. Bertrand, H. El Sukkari, J.-P. Gesson and B. Renoux, Synthesis, 1999, 330.
144. T. Saleh and G. Rousseau, Synlett, 1999, 617.
145. M. E. Jung, U. Karama and R. Marquez, J. Org. Chem., 1999, 64, 663.
146. S. H. Kang and S. B. Lee, Chem. Commun., 1998, 761.
147. J. M. Aurrecoechea and M. Solay, Tetrahedron, 1998, 54, 3851.
148. H. Takada, Y. Nishibayashi and S. Uemura, J. Chem. Soc., Perkin Trans. 1, 1999, 1511.
149. T. G. Back, B. P. Dyck and S. Nan, Tetrahedron, 1999, 55, 3191.
150. T. Wirth, Tetrahedron, 1999, 55, 1.
151. G. Fragale and T. Wirth, Eur. J. Org. Chem., 1998, 1361;
152. T. Wirth, G. Fragale and M. Spichty, J. Am. Chem. Soc., 1998, 120, 3376.
153. M. Tiecco, L. Testaferri and C. Santi, Eur. J. Org. Chem., 1999, 797.
154. F. Bravo, M. Kassou and S. Castillón, Tetrahedron Lett., 1999, 40, 1187.
155. M. Gruttadáuria, P. L. Meo and R. Noto, Tetrahedron, 1999, 55, 4769.
156. P. Li, T. Wang, T. Emge and K. Zhao, J. Am. Chem. Soc., 1998, 120, 7391.
157. P. Li, J. Yang and K. Zhao, J. Org. Chem., 1999, 64, 2259.
158. K. Nacro, M. Baltas, C. Zedde, L. Gorrichon and J. Jaud, Tetrahedron, 1999, 55, 5129.
159. M. Sasaki, T. Maruyama, R. Sakai and K. Tachibana, Tetrahedron Lett., 1999, 40, 3195.
160. Y. Mori, T. Sawada and H. Furukawa, Tetrahedron Lett., 1999, 40, 731.
161. M. Ahmar, C. Duyck and I. Fleming, J. Chem. Soc., Perkin Trans. 1, 1998, 272l.
162. I. Fleming and S. K. Ghosh, J. Chem. Soc, Perkin Trans, 1, 1998, 2733.
163. U. Meiners, E. Cramer, R. Fröhlich, B. Wibbeling and P. Metz, Eur. J. Org. Chem., 1998, 2073.
164. S. Usui and L. A. Paquette, Tetrahedron Lett., 1999, 40, 3495.
165. K. Fukatsu, N. Fujii and S. Ohkawa, Tetrahedron: Asymmetry, 1999, 10, 1521.
166. J. G. Urones, I. S. Marcos, N. M. Garrido, P. Basabe, S. G. San Feliciano, R. Coca and D. Díez, Synlett, 1998, 1365.
167. R. F. de la Pradilla, C. Montera, J. Priego and L. A. MartinezCruz, J. Org. Chem., 1998, 63, 9612.
168. W.-M. Dai and M. Y. H. Lee, Tetrahedron, 1998, 54, 12497.
169. For further elaboration of such compounds, see G. L. Edwards and D. J. Sinclair, Tetrahedron Lett., 1999, 40, 3933.
170. K. S. Feldman and M. S. Bruendl, Tetrahedron Lett., 1998, 39, 2911.
171. S. Schabbert and E. Schaumann, Eur. J. Org. Chem., 1998, 1873.
172. R. J. Boffey, M. Santagostino, W. G. Whittingham and J. D. Kilburn, Chem. Commun., 1998, 1875.
173. J. Tang, H. Shinokubo and K. Oshima, Synlett, 1998, 1075;
174. J. Tang, H. Shinokubo and K. Oshima, Tetrahedron, 1999, 55, 1893.
175. J. A. Murphy, F. Rasheed, S. J. Roome, K. A. Scott and N. Lewis, J. Chem. Soc, Perkin Trans. I, 1998, 2331.
176. X. Du and R. W. Armstrong, Tetrahedron Lett., 1998,39, 2281.
177. S. Berteina and A. De Mesmaeker, Tetrahedron Lett., 1998, 39, 5759.
178. P. Diaz, F. Gendre, L. Stella and B. Charpentier, Tetrahedron, 1998, 54, 4579.
179. S. R. Graham, J. A. Murphy and D. Coates, Tetrahedron Lett., 1999,40,2415.
180. D. J. Dixon, S. V. Ley.-T. Gracza and P. Szolcsanyi, J. Chem. Soc., Perkin Trans. 1, 1999,839.
181. Alkoxycarbonylation has also been used to prepare frenolicin B: P. Contant, M: Haess, J. Riegl, M. Scalone and M.Visnik, Synlett, 1999, 821.
182. C. Bittner, A. Burgo, P. J. Murphy, C. H. Sung and A. J. Thornhill, Tetrahedron Lett., 1999, 40, 3455.
183. For related intermolecular Wittig reactions of lactones and amides, see G. Sabitha, M. M. Reddy, D. Srihivas and J. S. Yadov, Tetrahedron Lett., 1999,40, 165.
184. S. R. Gilbertson and G. S. Hoge, Tetrahedron Lett., 1998, 39, 2075.
185. K. Kumar and R. S. Jolly, Tetrahedron Lett.,-1998,39, 3047.
186. A. Deagostino, C. Prandi and P. Venturello, Synthesis, 1998, 1149.
187. Y. Yamamoto, H. Kitahara, R. Ogawa and K. Itoh, J. Org. Chem., 1998, 63, 9610.
188. C. W. Holzapfel, L. Marais and F. Toerien, Tetrahedron, 1999, 55, 3467.
189. For a similar nickel-catalysed reaction, see B. Radetich and T. V. RajanBabu, J. Am. Chem. Soc., 1998, 120, 8007.
190. J.-G. Shim and Y. Yamamoto, J. Org. Chem., 1998, 63, 3067.
191. G. Mann, C. Incarvito, A. L. Rheingold and J. F. Hartwig, J. Am. Chem. Soc., 1999, 121, 3224.
192. Y. Uozumi, H. Kyota, K. Kato, M. Ogasawara and T. Hayashi, J. Org. Chem., 1999,64, 1620.
193. Y. Wang and T.-N. Huang, Tetrahedron Lett., 1998, 39, 9605.
194. R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413.
195. D. S. La, J. B. Alexander, D. R. Cefalo, D. D. Graf, A. H. Hoveyda and R. R. Schrock, J. Am. Chem. Soc., 1998, 120, 9720.
196. D. J. Aldous, W. M. Dutton and P. G. Steel, Synlett, 1999, 474.
197. R. C. D. Brown and J. D. Hinks, Chem. Commun., 1998, 1895.
198. M. A. Caller and C. Zhu, J. Org. Chem., 1999, 64, 1415.
199. S. R. Angle, D. S. Bernier, N. A. El-Said, D. E. Jones and S. Z. Shar, Tetrahedron Lett., 1998, 39, 3919.
200. S. R. Angle, D. S. Bernier, K. Chann, D. E. Jones, M. Kim, M. L. Nietzel and S. L. White, Tetrahedron Lett., 1998, 39, 8195.
201. G. A. Molander and J. Haas, Tetrahedron, 1999, 55, 617.
202. R. Rodriguez, A. Rumbo, L. Castedo and J. L. Mascarenas, J. Org. Chem., 1999, 64, 4560.
203. R. Di Florio and M. A. Rizzacasa, J. Org. Chem., 1998, 63, 8595.
204. M. Carda, E. Castillo, S. Rodriguez, E. Falomir and J. A. Marco, Tetrahedron Lett., 1998, 39, 8895.
205. D. Egron, T. Durand, A. Roland, J.-P. Vidai and J.-C. Rossi, Synlett, 1999, 435.
206. T. J. Donohoe, M. Helliwell, C. A. Stevenson and T. Ladduwahetty, Tetrahedron Lett., 1998, 39, 3071.
207. Q. Yu, Y. Wu, H. Ding and Y.-L. Wu, J. Chem. Soc., Perkin Trans, 1, 1999, 1183.
208. The same group have also prepared corossolin: Q. Yu, Z.-J. Yao, X.-G. Chen and .Y.-L. Wu, J. Org. Chem., 1999, 64, 2440.
209. H. Makabe, A. Tanaka and T. Oritani, Tetrahedron, 1998, 54, 6329.
210. Z.-M. Wang, S.-K. Tian and M. Shi, Tetrahedron: Asymmetry, 1999, 10, 667.
211. Z.-M. Wane, S.-K. Tian and M. Shi, Tetrahedron Lett., 1999, 40, 977.
212. J. A. Marshall and H. Jiang, J. Org. Chem., 1999, 64, 971;
213. J. A. Marshall and H. Jiang, J. Org. Chem., 1998, 63, 7066.
214. P. A. Evans and V. S. Murthy, Tetrahedron Lett., 1999, 40, 1253.
215. S. Bäurle, S. Hoppen and U. Koert, Angew: Chem., Int. Ed., 1999, 38, 1263.
216. S. Takahashi and T. Nakata, Tetrahedron Lett., 1999, 40, 723;
217. S. Takahashi and T. Nakata, Tetrahedron Lett., 1999, 40, 727.
218. P. Neogi, T. Doundoulakis, A. Yazbak, S. C. Sinha, S. C. Sinha and E. Keinan, J. Am. Chem. Soc., 1998, 120, 11279.
219. A. Sinha, S. C. Sinha, S. C. Sinha and E. Keinan, J. Org. Chem., 1999, 64, 2381.
220. S. C. Sinha, A. Sinha, S. C. Sinha and E. Keinan, J. Am. Chem. Soc., 1998, 120, 4017.
221. S. C. Sinha, E. Keinan and S. C. Sinha, J. Am. Chem. Soc., 1998, 120, 9076.
222. Z. Ruan and D. R. Mootoo, Tetrahedron Lett., 1999, 40, 49.
223. K. Li, S. Vig and F. M. Uckun, Tetrahedron Lett., 1998, 39, 2063.
224. For a related epoxide building block, see S.-T. Jan, K. Li, S. Vig, A. Rudolph and F. M. Uckun, Tetrahedron Lett., 1999, 40, 193.
225. D. R. Kelly and J. Nally, Tetrahedron Lett., 1999, 40, 2209.
226. J.-P. Gesson, B. Renoux and I. Tranoy, Tetrahedron, 1998, 54, 6739.
227. C. J. Forsyth, F. Ahmed, R. D. Cink and C. S. Lee, J. Am. Chem. Soc., 1998,120,5597.
228. I. Paterson, K.-S. Yeung, C. Watson, R. A. Ward and P. A. Wallace, Tetrahedron, 1998,54, 11935;
229. I. Paterson, C. Watson, K.-S. Yeung, R. A. Ward and P. A. Wallace, Tetrahedron, 1998, 54, 11955.
230. S. D. Rychnovsky, Y. Hu and B. Ellsworth, Tetrahedron Lett., 1998, 39,7271.
231. P. Wolbers and H. M. R. Hoffmann, Tetrahedron, 1999, 55, 1905.
232. D. R. Williams, M. P. Clark and M. A. Berliner, Tetrahedron Lett., 1999, 40, 2287.
233. I. Paterson and I. A. Arnott, Tetrahedron Lett., 1998, 39, 7185.
234. For the synthesis of a lactol ether corresponding to this tetrahydropyran ring, see P. Wolbers, A: M. Misske and H. M. R. Hoffmann, Tetrahedron Lett., 1999, 40, 4527.
235. I. Kadoto, C.-H. Park, M. Ohtaka, N. Oguro and Y. Yamamoto, Tetrahedron Lett., 1998, 39, 6365.,
236. G. C. Micalizio and W. R. Roush, Tetrahedron Lett., 1999, 40, 3351.
237. For a review of the spongistatins, see J. Pietruszka, Angew. Chem., Int. Ed., 1998, 37, 2629.
238. S. M. Dankwardt, J. W. Dankwardt and R. H. Schlessinger, Tetrahedron Lett., 1998, 39, 4971;
239. S. M. Dankwardt, J. W. Dankwardt and R. H. Schlessinger, Tetrahedron Lett., 1998, 39, 4975;
240. S. M. Dankwardt, J. W. Dankwardt and R. H. Schlessinger, Tetrahedron Lett., 1998, 39, 4979;
241. S. M. Dankwardt, J. W. Dankwardt and R. H. Schlessinger, Tetrahedron Lett., 1998, 39, 4983.
242. S. V. Ley, A. C. Humphries, H. Eick, R. Downham, A. R. Ross, R. J. Boyce, J. B. J. Pavey and J. Pietruszka, J. Chem. Soc., Perkin Trans, 1, 1998, 3907.
243. For an application of this chemistry to fragments of Altohyrtin A, see E. Fernandez-Megia, N. Gourlaouen, S. V. Ley and G. J. Rowlands, Synlett, 1998, 991.
244. S. V. Ley, D. S. Brown, J. A. Clase, A. J. Fairbanks, I. C. Lennon, H. M. I. Osborn, E. S. E. Stokes and D. J. Wadsworth, J. Chem. Soc., Perkin Trans, 1, 1998, 2259.
245. J.-P. Surivet and J.-M. Vatèle, Tetrahedron Lett., 1998, 39, 9681.
246. For an earlier, related, approach, see J.-P. Surivet and J.-M. Vatèle, Tetrahedron Lett., 1998, 39, 7299.
247. For other approaches to compounds of this class, see M. Tsubuki, K. Kanai, H. Nagase and T. Honda, Tetrahedron, 1999, 55, 2493.
248. R. J. Maguire, S. P. Munt and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1998, 2853.
249. D. A. Evans, P. H. Carter, E. M. Carreira, J. A. Prunet, A. B. Charette and M. Lautens, Angen: Chem., Int. Ed., 1998, 37, 2354.
250. For an identical approach to tetrahydropyran formation, see L. A. Paquette, L. Barriault and D. Pissarnitski, J. Am. Chem. Soc., 1999, 121, 4542.
251. S. E. Schaus, J. Brånalt and E. N. Jacobsen, J. Org. Chem., 1998, 63, 4876.
252. K. Chiba, T. Hirano, Y. Kitano and M. Tada, Chem Commun., 1999, 691.
253. For an electrochemical method from the same group, see K. Chiba, Y. Yamaguchi and M. Tada, Tetrahedron Lett., 1998, 39, 9035.
254. For a further similar example, see K. Tatsuta, T. Tamura and T. Mase, Tetrahedron Lett., 1999, 40, 1925.
255. M. Johannsen and K. A. Jorgensen, J. Org. Chem., 1999, 64,299.
256. T. A. Adams, M. E. Welker and C. S. Day, J. Org. Chem., 1998,63, 3683.
257. J. Thorhauge, M. Johannsen and K. A. Jorgensen, Angew. Client., Int. Ed., 1998,37,2404.
258. S. Yao, M. Johannsen, H. Audrain, R. G. Hazell and K. A. Jorgensen, J. Am. Chem. Soc., 1998,120, 8599.
259. D. A. Evans, E. J. Olhava, J. S. Johnson and J. M. Janey, Angew. Chem., Int. Ed., 1998,37, 3372.
260. A. Mann, C. Muller and E. Tyrell, J. Chem. Soc., Perkin Trans, l, 1998, 1427.
261. R. C. Larock, Y. He, W. W. Leong, X. Han, M. D. Refvik and J. M. Zenner, J. Org. Chem., 1998, 63, 2154.
262. R. C. Larock, L. Wei and T. R. Hightower, Synlett, 1998, 522.
263. R. C. Larock, H. Yang, P. Pace, K.,Narayanan, C. E. Russell, S. Cacchi and G. Fabrizi, Tetrahedron, 1998,54, 7343.
264. A. F. Barrero, E. J. Alvarez-Manzaneda, R. Chahboun. and M. C. Paiz, Tetrahedron Lett., 1998, 39, 9543.
265. S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 1999,40, 1747.
266. B. M. Trost and F. D. Toste, J. Am. Chem. Soc., 1998,120,9074.
267. D. W. Knight and P. B. Little, Tetrahedron Lett., 1998,39, 5105.
268. D. W. Knight and P. B. Little, Synlett, 1998, 1141.
269. J. D. White, J. Hong and L. A. Robarge, Tetrahedron Lett., 1999, 40, 1463.
270. J. L. Bowman and F. E. McDonald, J. Org. Chem., 1998, 63,3680.
271. F. E. McDonald and P. Vadapally, Tetrahedron Lett., 1999, 40, 2235.
272. N. Hori, H. Matsukura, G. Matsuo and T. Nakata, Tetrahedron Lett., 1999,40,2811.
273. J. S. Clark, G. P. Trevitt, D. Boyall and B. Stammen, Chem. Commun., 1998, 2629.
274. M. Picquet, C. Brunneau and P. H. Dixneuf, Chem. Commun., 1998,2249. . .
275. J. D. Rainier and S. P. Allwein, J. Org. Chem., 1998, 63, 5310.
276. J. D. Rainier and S. P. AlKvein, Tetrahedron Lett., 1998, 39, 9601.
277. C. F. Sturino and J. C. Y. Wona, Tetrahedron Lett., 1998, 39, 9623.
278. D. M. Hodgson, A. M. Foley and P. J. Lovell, Synlett, 1999, 744.
279. M. E. Maier and M. Bugl, Synlett, 1998, 1390.
280. S. D. Burke, R. A. Ng, J. A. Morrison and M. J. Albert!, J. Org. Chem., 1998,63, 3160.
281. S. D. Burke, K. J. Quinn and V. J. Chen, J. Org. Chem., 1998, 63, 8626.
282. C. W. Johannes, M. S. Visser, G. S. Weatherhead and A. H. Hoveyda, J. Am. Chem. Soc., 1998,120, 8340.
283. B. Schmidt, Tetrahedron Lett., 1999,40,4319.
284. S. Hosokawa, B. Kirschbaum and M. Isobe, Tetrahedron Lett., 1998,39,1917.
285. J. M. Bailey, D. Craig and P. T. Gallagher, Synlett, 1999, 132.
286. D. Craig, A. H. Payne and P. Warner, Tetrahedron Lett., 1998,39, 8325;
287. I. P. Smoliakova, M. Han, J. Gong, R. Caple and W. Smit, Tetrahedron, 1999, 55,4559.
288. A. K. Ghosh and R. Kawahama, Tetrahedron Lett., 1999, 40, 1;
289. A. K. Ghosh and R. Kawahama, Tetrahedron Lett., 1999,40,4751.
290. G. E. Keck and G. D. Lundquist, J. Org. Chem., 1999, 64,4482.
291. P. D. Kary, S. M. Roberts and D. J. Watson, Tetrahedron: Asymmetry, 1999, 10, 213;
292. P. D. Kary and S. M. Roberts, Tetrahedron: Asymmetry, 1999, 10, 217.
293. H. Nakamura, M. Takahashi and A. Murai, Tetrahedron: Asymmetry, 1998, 9, 2571.
294. M. F. Buffet, D. J. Dixon, S. V. Ley and E. W. Tate, Synlett, 1998, 1091.
295. D. J. Dixon, S. V.- Ley and E. W: Tate, Synlett, 1998, 1093.
296. T. Nishikawa, M. Ishikawa and M. Isobe, Synlett, 1999, 123.
297. N. Maezaki, Y. Matsumori, T. Shogaki, M. Soejima, H. Ohishi, T. Tanaka and C. Iwata, Tetrahedron, 1998,54, 13087.
298. L. Lemée, A. Jégou and A. Veyrières, Tetrahedron Lett., 1999, 40, 2761.
299. M. Sugawara and J.-I. Yoshida, Tetrahedron Lett., 1999, 40, 1717.
300. J. Yang and C.-J. Li, Synlett, 1999, 717;
301. J. Yang, G. S. Viswanathan and C.-J. Li, Tetrahedron Lett., 1999, 40, 1627.
302. M. J. Clonincer and L. E. Overman, J. Am. Chem. Soc., 1999, 121, 1092.
303. M. Suginome, T. Iwanami and Y. Ito, J. Org. Chem., 1998, 63, 6096.
304. Y. Takemoto, T. Ibuka, H. Hayase, A. Iwanaga, S. Yamagata, C. Iwata and T. Tanaka, Tetrahedron Lett., 1998/39, 7545.
305. N. Edwards, J. A. Macritchie and P. J. Parsons, Tetrahedron Lett., 1998,39,3605.
306. M. E. June, B. T. Fahr and D. C. D'Amico, J. Org. Chem., 1998,63, 2982.
307. J. O. Hoberg, Tetrahedron, 1998,54, 12631.
308. G. A. Molander, Ace. Chem. Res., 1998,31,603.
309. T. Oishi, M. Maruyama, M. Shoji, K. Maeda, N. Kumahara, S.-I. Tanaka and M. Hirama, Tetrahedron, 1999,55, 7471.
310. I. Kadota and Y. Yamamoto, J. Org. Chem., 1998,63, 6597.
311. Y. Mori, K. Yaegashi and H. Furukawa, J. Org. Chem., 1998, 63, 6200.
312. I. Kadota, C. Kadowaki, N. Yoshida and. Y. Yamamoto, Tetrahedron Lett., 1998, 39, 6369.
313. I. Kadota, A. Ohno, Y. Matsukawa and Y. Yamamoto, Tetrahedron Lett., 1998, 39, 6373.
314. J.-Y. Park, I. Kadota and Y. Yamamoto, J. Org. Chem., 1999, 64, 4901.
315. M. Isobe, R. Nishizawa, S. Hosokawa and T. Nishikawa, Chem. Commun., 1998, 2665.
316. R. Saeeng and M. Isobe, Tetrahedron Lett., 1999, 40, 1911.
317. For closely related work, see S. Hosokawa and M. Isobe, J. Org. Chem., 1999, 64, 37.
318. For another recently isolated member of this family, see R. J. Lewis, J.-P. Vernoux and I. M. Brereton, J. Am. Chem. Soc., 1998, 120, 5914.
319. K. Maeda, T. Oishi, H. Oguri and M. Hirama, Chem. Commun., 1999, 1063.
320. T. Oishi, Y. Nagumoand M. Hirama, Chem. Commun., 1998, 1041.
321. For another RCM approach to medium and large rings, see M. Delgado and J. D. Martin, J. Org. Chem., 1999, 64, 4798.
322. M. Sasaki, M. Inoue, T. Noguchi, A. Takeichi and K. Tachibana, Tetrahedron Lett., 1998, 39, 2783;
323. M. Sasaki, T. Noguchi and K. Tachibana, Tetrahedron Lett., 1999, 40, 1337.
324. K. Fujiwara, :D. Awakura, M. Tsunashima, A. Makamura, T. Honma and A. Murai, J. Org. Chem., 1999, 64, 2616.
325. M. T. Mujica, M. M. Afonso, A. Galindo and J. A. Palenzuela, J. Org. Chem, 1998, 63, 9728.
326. M. T. Crimmins and A. L. Choy, J. Am. Chem. Soc., 1999, 121, 5653.
327. S. D. Edwards, T. Lewis and R. J. K. Taylor, Tetrahedron Lett., 1999, 40, 4267.
328. J. S. Clark, O. Hamelin and R. Hufton, Tetrahedron Lett., 1998, 39, 8321.
329. R. Grigg, V. Sridharan and M. York, Tetrahedron Lett., 1998, 39, 4139.
330. M. Stefinovic and V. Snieckus, J. Org. Chem., 1998, 63, 2808.
331. C. Baylon, M.-P. Heck and C. Mioskowski, J. Org. Chem., 1999, 64, 3354.
332. N. Hori, K. Nagasawa, T. Shimizu and T. Nakata, Tetrahedron Lett., 1999, 40, 2145.
333. J. S. Clark, A. G. Dossetter, A. J. Blake, W.-S. Li and W. G. Whittingham, Chem. Commun., 1999, 749.
334. R. W. Tester and F. G. West, Tetrahedron Lett., 1998,39,4631.
335. S. Robin and G. Rousseau, Tetrahedron Lett., 1998, 39, 2759.
336. For related chemistry, see F. Simart, Y. Brunei, S. Robin and G. Rousseau, Tetrahedron, 1998,54, 13557.