Enantioselective allyltitanation. Application to the synthesis of lactone units related to compactin and mevinolin

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3363-3366

  Bouzbouz, Samir ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

1,3 diols; Allyltitanation; Compactin; Lactones; Mevinolin

Indexed keywords

ALDEHYDE; COMPACTIN; LACTONE; MEVINOLIN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; ENANTIOMER; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034728852     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00451-2     Document Type: Article

References (28)

1. (a) Brown, A. G.; Smale, T. C.; King, T. J.; Hasenkamp, R.; Thompson, R. H. J. Chem. Soc., Perkin Trans. 1 1976, 1165-1170;
2. (b) Endo, A.; Kuroda, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346-1348;
3. (c) Endo, A. J. Antibiot. 1979, 32, 852-854.
4. Jendralla, H.; Granzer, E.; von Kerekjarto, B.; Krause, R.; Schacht, U.; Baader, E.; Bartmann, W.; Beck, G.; Bergmann, A.; Kesseler, K.; Wess, G.; Chen, L. J.; Granata, S.; Herchen, J.; Kleine, H.; Schussler, H.; Wagner, K. J. Med. Chem. 1991, 34, 2962-2983.
5. Drugs of the Future 1987, 12, 437-442.
6. Minami, T.; Takahashi, K.; Hiyama, T. Tetrahedron Lett. 1993, 34, 513-516.
7. (a) Hanessian, S.; Roy, P. J.; Petrini, M.; Hodges, P. J.; Di Fabio, R.; Carganico, G. J. Org. Chem. 1990, 55, 5766-5777;
8. (b) Menges, M.; Brückner, R. Synlett 1993, 901-905.
9. Majewski, M.; Clive, D. L. J.; Anderson, P. C. Tetrahedron Lett. 1984, 25, 2101-2104.
10. (a) Miyazawa, K.; Yoshida, N. Chem. Lett. 1993, 1529-1530;
11. (b) Ermolenko, M. S.; Olesker, A.; Lukas, G. Tetrahedron Lett. 1994, 35, 711-714 and 715-718;
12. (c) Roth, B. D.; Roark, W. H. Tetrahedron Lett. 1988, 29, 1255-1258.
13. Terada, M.; Mikami, K.; Nakai, T. Tetrahedron Lett. 1991, 32, 935-938.
14. Lynch, J. E.; Volante, R. P.; Wattley, R. V.; Shinkai, I. Tetrahedron Lett. 1987, 28, 1385-1388.
15. Bonadies, F.; Di Fabio, R.; Gubbiotti, A.; Mecozzi, S.; Bonini, C. Tetrahedron Lett. 1987, 28, 703-706.
16. (a) Shao, L.; Seki, T.; Kawano, H.; Saburi, M. Tetrahedron Lett. 1991, 32, 7699-7702;
17. (b) Bennett, F.; Knight, D. W.; Fenton, G. J. Chem. Soc., Perkin Trans. 1 1991, 133-140;
18. (c) Ansari, M. H.; Kusumoto, T.; Hiyama, T. Tetrahedron Lett. 1993, 34, 8271-8274.
19. Compound (+)-6 is showing all the characteristics described in the literature: Rychnovsky, S. D.; Griesgraber, G.; Zeller, S.; Skalitzky, D. J. J. Org. Chem. 1991, 56, 5161-5169.
20. Solladié, G.; Bauder, C.; Rossi, L. J. Org. Chem. 1995, 60, 7774-7777.
21. Honda, T.; Ono, S.; Mizutani, H.; Hallinan, K. O. Tetrahedron: Asymmetry 1997, 8, 181-184.
22. (a) Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321-2336.
23. (b) BouzBouz, S.; Cossy, J. Org. Lett. 2000, 2, 501-504.
24. This reaction was achieved on 0.2 g of 1 and on 0.5 g of 7.
25. The enantiomeric excess of 8 and 12 was determined by HPLC analysis, Chiralcel-AD2 column (hexane:isopropanol).
26. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948.
27. Preparation of compound 7:
28. +) calcd for C12H12O4Cl3 (M+1) 324.9801. Found 324.9799.