Studies on Wittig rearrangement of furfuryl ethers in steroidal side chain synthesis

Tetrahedron

Volumn 61, Issue 5, 2005, Pages 1095-1100

  Tsubuki, Masayoshi ^a   Ohinata, Akira ^a   Tanaka, Tomoaki ^a   Takahashi, Kazunori ^a   Honda, Toshio ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

22 Hydroxy steroid; Furfuryl carbinol; Furfuryl ether; Wittig rearrangement

Indexed keywords

ETHER DERIVATIVE; ETHYLENE DERIVATIVE; FURFURYL ALCOHOL; HYDROXYL GROUP; METHYL GROUP; STEROID;

ARTICLE; ENERGY YIELD; HYDROGENATION; ISOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 12344271169     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.055     Document Type: Article

References (36)

1. For recent reviews, see (a) J.A. Marshall B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 3 1991 Pergamon New York 975 1014
2. R. Brückner B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 6 1991 Pergamon New York 873 908
3. T. Nakai, and K. Mikami Org. React. 46 1994 105 209
4. T. Nakai, and K. Tomooka Pure Appl. Chem. 69 1997 595 600
5. K. Tomooka Z. Rappoport I. Marek The Chemistry of Organolithium Compounds 2004 Wiley New York 749 828
6. M. Tsubuki, H. Okita, and T. Honda Chem. Commun. 1995 2135 2136
7. M. Tsubuki, T. Kamata, H. Okita, M. Arai, A. Shigihara, and T. Honda Chem. Commun. 1999 2263 2264
8. T. Kametani, M. Tsubuki, H. Furuyama, and T. Honda Chem. Commun. 1984 375 376
9. T. Kametani, M. Tsubuki, K. Higurashi, and T. Honda J. Org. Chem. 51 1986 2932 2939
10. T. Honda, K. Keino, and M. Tsubuki Chem. Commun. 1990 650 651
11. M. Tsubuki, K. Keino, and T. Honda J. Chem. Soc., Perkin Trans. 1 1992 2643 2649
12. M. Tsubuki, K. Kanai, K. Keino, N. Kakinuma, and T. Honda J. Org. Chem. 57 1992 2930 2934
13. M. Tsubuki, H. Takada, T. Katoh, S. Miki, and T. Honda Tetrahedron 46 1996 14515 14532
14. K. Mikami, K. Kawamoto, and T. Nakai Chem. Lett. 1985 1719 1722
15. K. Mikami, K. Kawamoto, and T. Nakai Tetrahedron Lett. 26 1985 5799 5802
16. K. Mikami, K. Kawamoto, and T. Nakai Tetrahedron Lett. 27 1986 4899 4902
17. M. Koreeda, and D.J. Ricca J. Org. Chem. 51 1986 4090 4092
18. L. Castedo, J.R. Granja, and A. Mourino Tetrahedron Lett. 26 1985 4959 4960
19. L. Castedo, J.R. Granja, A. Mourino, and M.C. Pumar Synth. Commun. 17 1987 251 256
20. M. Tanabe, and K. Hayashi J. Am. Chem. Soc. 102 1980 862 863
21. N.R. Schmuff, and B.M. Trost J. Org. Chem. 48 1983 1404 1412
22. W.R. Kirner J. Am. Chem. Soc. 50 1928 1955 1961
23. S. Divald, M.C. Chun, and M.M. Joullie J. Org. Chem. 41 1976 2835 2846
24. P.C. Brookes, P.J. Murphy, K. Sommer, D.E. Hibbs, M.B. Hursthouse, and K.M.A. Malik J. Chem. Soc., Perkin Trans. 1 1998 1899 1901
25. The radical mechanism for [2,3]Wittig rearrangement was also supported: T. Itoh, and K. Kudo Tetrahedron Lett. 42 2001 1317 1320
26. T. Kametani, T. Katoh, J. Fujio, I. Nogiwa, M. Tsubuki, and T. Honda J. Org. Chem. 53 1988 1982 1991
27. For synthetic studies toward OSW-1, see, e.g., (a) C. Guo, and P.L. Fuchs Tetrahedron Lett. 39 1998 1099 1102
28. S. Deng, B. Yu, Y. Lou, and Y. Hui J. Org. Chem. 64 1999 202 208
29. J.W. Morzycki, A. Gryszkiewicz, and I. Jastrzebska Tetrahedron 57 2001 2185 2193
30. W. Yu, and Z. Jin J. Am. Chem. Soc. 124 2002 6576 6583
31. Q.-H. Xu, X.-W. Peng, and W.-S. Tian Tetrahedron Lett. 44 2003 9375 9377
32. B. Shi, B. Yu, and J. Wu Angew. Chem., Int. Ed. 43 2004 4327
33. For synthetic studies toward cephalostatins, see, e.g., (a) S. Kim, S.C. Sutton, C. Guo, T.G. LaCour, and P.L. Fuchs J. Am. Chem. Soc. 121 1999 2056 2070
34. J.K. Jeong, C. Guo, and P.L. Fuchs J. Am. Chem. Soc. 121 1999 2071 2084
35. W. Li, T.G. LaCour, and P.L. Fuchs J. Am. Chem. Soc. 124 2002 4548 4549
36. W. Li, and P.L. Fuchs Org. Lett. 5 2003 2849 2852