Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1323-1340

  Shing, Tony K M ^a   Wong, Ching Hung ^a   Yip, Ting ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

OXEPANE DERIVATIVE; UNCLASSIFIED DRUG; ZOAPATANOL;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029953154     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00149-8     Document Type: Article

References (40)

1. Y. Oshima, G. A. Cordial and H. S. Fong, Phytochemistry, 1986, 25, 2567. L. Quijano, J. S. Calderon and N. K. Fisher, Phytochemistry, 1985, 24, 2337.
2. Y. Oshima, G. A. Cordial and H. S. Fong, Phytochemistry, 1986, 25, 2567. L. Quijano, J. S. Calderon and N. K. Fisher, Phytochemistry, 1985, 24, 2337.
3. R. M. Konojia, E. Chin, C. Smith, R. Chen, D. Rowand, S. D. Levine, M. P. Wachter, R. E. Adams and D. W. Hahn, J. Med. Chem., 1985, 28, 796. D. W. Hahn, E. W. Ericson, M. T. Lai, and A. Probst, Contraception, 1981, 23, 133. D. W. Hahn, A. J. Tobia, H. E. Rosenthale, and J. L. McGuire, Contraception, 1984, 26, 133.
4. R. M. Konojia, E. Chin, C. Smith, R. Chen, D. Rowand, S. D. Levine, M. P. Wachter, R. E. Adams and D. W. Hahn, J. Med. Chem., 1985, 28, 796. D. W. Hahn, E. W. Ericson, M. T. Lai, and A. Probst, Contraception, 1981, 23, 133. D. W. Hahn, A. J. Tobia, H. E. Rosenthale, and J. L. McGuire, Contraception, 1984, 26, 133.
5. R. M. Konojia, E. Chin, C. Smith, R. Chen, D. Rowand, S. D. Levine, M. P. Wachter, R. E. Adams and D. W. Hahn, J. Med. Chem., 1985, 28, 796. D. W. Hahn, E. W. Ericson, M. T. Lai, and A. Probst, Contraception, 1981, 23, 133. D. W. Hahn, A. J. Tobia, H. E. Rosenthale, and J. L. McGuire, Contraception, 1984, 26, 133.
6. J. B. Smith, E. F. Smith, A. M. Lefer and K. C. Nicolaou, Life Sciences, 1981, 28, 2743.
7. S. D. Levine, R. E. Adams, R. Chen, M. L. Lottar, A. F. Hirsch, V. V. Kane, R. M. Kanojia, C. Shaw, M. P. Wachter, E. Chin, R. Huettemann, P. Ostrowski, J. L. Mateos, L. Noriega, A. Guzman, A. Mijarez and L. Tovar, J. Am. Chem. Soc., 1979, 101, 3404.
8. R. M. Konojia, M. P. Wachter, S. D. Levine, R. E. Adams, R. Chen, E. Chin, M. L. Lottar, A. F. Hirsch, R. Huttemann, V. V. Kane, P. Ostrowski, C. J. Shaw, J. L. Mateos, L. Noriega, A. Guzman, A. Mijarez, L. Tovar and E. Shefter, J. Org. Chem., 1982, 47, 1310.
9. R. C. Cookson and N. J. Liverton, J. Chem. Soc., Perkin Trans. 1, 1985, 1589.
10. R. Chen and D. A. Rowand, J. Am. Chem. Soc., 1980, 102, 6609.
11. K. C. Nicolaou, D. A. Clareman and W. E. Barnette, J. Am. Chem. Soc., 1980, 102, 6611.
12. P. J. Kocienski, C. J. Love and R. J. Whitby and D. A. Roberts, Tetrahedron Lett., 1988, 29, 2867. P. J. Kocienski, C. J. Love and R. J. Whitby, Tetrahedron, 1989, 45, 3839.
13. P. J. Kocienski, C. J. Love and R. J. Whitby and D. A. Roberts, Tetrahedron Lett., 1988, 29, 2867. P. J. Kocienski, C. J. Love and R. J. Whitby, Tetrahedron, 1989, 45, 3839.
14. V. V. Kane and D. L. Doyle Tetrahedron . Lett., 1981, 22, 3027, 3031.
15. B. M. Trost, P. D. Greenspan and H. Geissler, Angew Chem. Int. Ed. Engl. 1994, 33, 2182.
16. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
17. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
18. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
19. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
20. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
21. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
22. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
23. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
24. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
25. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
26. For methodologies towards the construction of oxepane rings, see, M. J. Davies, J. C. Heslin, and C. J. Moody, J. Chem. Soc., Perkin Trans. 1, 1989, 2473. L. Coppi, A Ricci and M. Taddei, J. Org. Chem., 1988, 53, 911. L. E. Overman, A. Castaneda and T. A. Blumenkopf, J. Am. Chem. Soc., 1986, 108, 1303. K. C. Nicolaou, C. V. C. Prasad, P. K. Somers and C. K. Hwang, J. Am. Chem. Soc., 1989, 111, 5335. P. L. Lopex-Tudanea, K. Jones and P. Brownbridge, Tetrahedron Lett., 1991, 32, 2261. P. Brownbridge, J. Chem. Soc., Chem. Commun., 1987, 1280. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1509; corrigenum, 1991, 136. P. M. Collins, M. S. Ashwood, H. Eder, S. M. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055. Y. Yamamoto, J.-I. Yamada and I. Kadota, Tetrahedron Lett., 1991, 32, 7069. W. T. Brady, Y-S. F. Giang, L. Went and M. M. Dad., J. Org. Chem., 1987, 52, 2216. K. C. Nicolaou, C. K. Hwang, M. E. Daggan, K. B. Reddy, B. E. Marron and D. G. McGarry, J. Am. Chem. Soc., 1986, 108, 6800.
27. Y. Gao, R. M. Hanson, J. M. Kluder, S. Y. Ko, H. Masamune and K. B. Sharpless J. Am. Chem. Soc., 1987, 109, 5765.
28. G. Desimoni, G. Taconni, A. Barco and G. P. Pollini,'Natural Products Synthesis Through Pericyclic Reactions', ACS Monograph 180, American Chemical Society, U. S. A., 1983. K. B. G. Torssell, 'Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis', VCH, U. S. A., 1988.
29. G. Desimoni, G. Taconni, A. Barco and G. P. Pollini,'Natural Products Synthesis Through Pericyclic Reactions', ACS Monograph 180, American Chemical Society, U. S. A., 1983. K. B. G. Torssell, 'Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis', VCH, U. S. A., 1988.
30. T. K. M. Shing and C.-H. Wong, Tetrahedron: Assymetry, 1994, 5, 1151.
31. T. K. M. Shing, W.-C. Fung and C.-H. Wong, J. Chem. Soc., Chem. Commun., 1994, 449; corrigenum, 1994, 1403.
32. O. T. Schmidt, Methods Carbohydr. Chem., 1965, 2, 319.
33. J. S. Brimacombe, A. J. Rollins and S. W. Thompson, Carbohydr. Res., 1973, 31, 108.
34. S. Czerneski, C. Georgoulis, C. L. Stevens and K. Vizayakumatan, Tetrahedron Lett., 1985, 26, 1699.
35. D. C. Baker, D. Horton and C. G. Tindall, Jr., Carbohydr. Res., 1972, 24, 192.
36. For a recent review, see T. K. M. Shing, in 'Comprehensive Organic Synthesis', eds. I. Flemming and B. M. Trost , Pergamon Press, Oxford, 1991, vol. 7, p. 703.
37. G. W. J. Fleet and T. K. M. Shing, J. Chem. Soc., Chem. Commun., 1984, 835.
38. P. J. Garegg and B. Samuelson, Synthesis, 1979, 469.
39. G. A. Lee, Synthesis, 1982, 508.
40. A. P. Kozikowski and P. D. Stein, J. Am. Chem. Soc., 1982, 104, 4023.