The Anionic [1,3]-H-Shift Applied in Synthesis: A Novel Access to (+)-Citreoviral

Advanced Synthesis and Catalysis

Volumn 342, Issue 8, 2000, Pages 773-778

  Mulzer, Johann ^a,c   Bilow, Jörn ^b   Wille, Gregor ^b  

^a Institute of Organic Chemistry   (Austria)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

Citreoviral; Cyclizations; Natural products; Synthetic methods; Tetrahydrofuran synthesis

Indexed keywords

EID: 0346108620     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Y. Hirata, J. Chem. Soc. Jpn 1947, 65, 63
2. a) Y. Uleno in Mycotoxines, Hrsg.: I. F. H. Purchase, Elsevier, New York 1974, 283;
3. b) Ch. Zink, Pschyrembel Klinisches Wörterbuch, 256. ed., W. de Gruyter, Berlin 1990, 194
4. P. Mitchell, FEBS Lett. 1977, 78, 1
5. Y. Shizuri, S. Nishiyama, D. Imai, S. Yamamura, Tetrahedron Lett. 1984, 25, 4771
6. D. R. Williams, F. H. White, Tetrahedron Lett. 1985, 26, 2529, J. Org. Chem. 1987, 52, 5067
7. D. R. Williams, F. H. White, Tetrahedron Lett. 1985, 26, 2529, J. Org. Chem. 1987, 52, 5067
8. a) S. Nishiyama, Y. Shizuri, S. Yamamura, Tetrahedron Lett. 1985, 26, 231;
9. b) Shizuri, H. Suh, C. S. Wilcox, J. Am. Chem. Soc. 1988, 110, 470;
10. c) K. Wang, H. Venkataraman, Y. G. Kim, J. K. Cha, J. Org .Chem. 1991, 56, 7174
11. a) S. Nishiyama, H. Shigemori, S. Yamamura, J. Chem. Soc., Chem. Commun. 1985, 292;
12. b) M. C. Bowden, P. Patel, G. Pattenden, Tetrahedron Lett. 1985, 26, 4793;
13. c) M. J. Begley, M. C. Bowden, P. Patel, G. Pattenden, J. Chem. Soc., Perkin Trans. I 1991, 1951;
14. d) W. Ebenezer, G. Pattenden, Tetrahedron Lett. 1992, 33, 4053
15. a) B. M.Trost, J. K. Lynch, S. R. Anlge, Tetrahedron Lett. 1987, 28, 375;
16. b) S. Hatakeyama, Y. Matsui, M. Suzuki, K. Sakurai, S. Takano, Tetrahedron Lett. 1985, 26, 6485;
17. c) S. Hatakeyama, K. Sakurai, H. Numata, N. Ochi, S. Takano, J. Am. Chem. Soc. 1988, 110, 5201;
18. d) N. Hanaki, J. T. Link, D. W. C. MacMillan, L. E. Overman, W. G. Trankle, J. A. Wurster, Org. Lett. 2000, 2, 223
19. J. Baldwin, J. Chem. Soc., Chem. Commun. 1976, 734
20. J. Mulzer, G. Wille, J. Bilow, D. Arigoni, B. Martinoni, K. Roten, Tetrahedron Lett. 1997, 38, 5469; cf. also J. Gigg, R. Gigg, J. Chem. Soc. C. 1968, 1903
21. J. Mulzer, G. Wille, J. Bilow, D. Arigoni, B. Martinoni, K. Roten, Tetrahedron Lett. 1997, 38, 5469; cf. also J. Gigg, R. Gigg, J. Chem. Soc. C. 1968, 1903
22. J. Mulzer, P. deLasalle, A. Freißler, Liebigs Ann. Chem. 1986, 1152
23. a) W. R. Roush, M. A. Adams, A. E. Walts, D. J. Harris, J. Am. Chem. Soc. 1986, 108, 3422;
24. b) J. Garcia, B. M. Kim, S. Masamune, J. Org. Chem. 1987, 52, 4831
25. W. C. Still, J. McDonald III, Tetrahedron Lett. 1980, 21, 1031; Review: R. M. Devant, H. E. Radunz in Houben-Weyl, Methods of Organic Chemistry, Vol. 21 b, Stereoselective Synthesis, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, editors), Thieme, Stuttgart, New York 1995, p. 1151 ff
26. W. C. Still, J. McDonald III, Tetrahedron Lett. 1980, 21, 1031; Review: R. M. Devant, H. E. Radunz in Houben-Weyl, Methods of Organic Chemistry, Vol. 21 b, Stereoselective Synthesis, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, editors), Thieme, Stuttgart, New York 1995, p. 1151 ff
27. J. K. Cha, W. J. Christ, Y. Kishi, Tetrahedron Lett. 1983, 24, 3943
28. a) S. Hanessian, Y. Guindon, Tetrahedron Lett. 1989, 21, 2305;
29. b) K. C. Nicolaou, M. R. Pavia, S. P. Seitz, J. Am. Chem. Soc. 1982, 104, 2027
30. K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136
31. T. Iversen, K. R. Bundle, J. Chem. Soc., Chem. Commun. 1981, 1240