A straightforward synthesis of protected isostatine from achiral precursors using the asymmetric chelate claisen rearrangement

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 479-482

  Kazmaier, Uli ^a   Krebs, Achim ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BETA HYDROXY GAMMA AMINO ACID ISOSTATINE; STATIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; DRUG USE; ENANTIOMER; IMMUNOSUPPRESSIVE TREATMENT;

EID: 0033556135     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02486-1     Document Type: Article

References (36)

1. a) U. Gräfe in Biochemie der Antibiotika, Spektrum, Heidelberg, 1992;
2. b) R. Henning in Organic Synthetic Highlights II, (H. Waldmann, Ed.), VCH. Weinheim, 1995, 251; and references cited therein.
3. H. Morishima, T. Takita, T. Aoyagi, T. Takeuchi, H. Umezawa, J. Antibiot. 1971, 23, 259.
4. G. R. Pettit, S. B. Singh, F. Hogan, P. Lloyd-Williams, D. Herald, D. D. Burkett, P- Clewlow, J. Am. Chem. Soc. 1989, 111, 5463.
5. R. Sakai, J. G. Stroh,. D. W. Sullins, K. L. Rinehart, J. Am. Chem. Soc. 1995, 117, 3734, and references cited.
6. R. Sakai, K. L. Rinehart, V. Kishore, B. Kundu, G. Faircloth, J. B. Gloer, J. R. Carney, M. Namikoshi, F. Sun, R. G. Hughes, JR., D. G. Gravalos, T. G. de Quasada, G. R. Wilson, R. M. Heid, J. Med. Chem. 1996, 39, 2819, and reference cited therein.
7. a) K. L. Rinehart, V. Kishore, S. Nagarajan, R. J. Lake, J. B. Gloer, F. A. Bozich, K.-M. Li, R. E. Maleczka, JR., W. L. Todsen, M. H. G. Munroe, D. W. Sullins, R. Sakai, J. Am. Chem. Soc. 1987, 109, 6846;
8. b) U. Schmidt, M. Kroner, H. Griesser, Tetrahedron Lett. 1988, 29, 3057;
9. c) Y. Hamada, Y. Kondo, M. Shibata, T. Shioiri, J. Am. Chem. Soc., 1989, 111,669;
10. d) P. Jouin, J. Poncet, M.-N. Dufour, A. Panataloni, B. Castro, J. Org. Chem. 1989, 54, 617;
11. e) W.-R Li, W. R. Ewing, B. D. Harris, M. M. Joullie, J. Am. Chem. Soc., 1990, 112, 7659.
12. a) B. D. Harris, M. M. Joullie, Tetrahedron 1988, 44, 3489;
13. b) U. Schmidt, M. Kroner, H. Griesser, Synthesis 1989, 832;
14. c) H. Kessler, M. Schudok, Synthesis 1990, 457;
15. d) K. R. Rinehart, R. Sakai, V. Kishore, D. W. Sullins, K.-M. Li, J. Org. Chem. 1992, 57, 3007;
16. e) P. Castejón, A. Moyano, M. A. Pericas, A. Riera, Chem. Eur. J. 1996, 1001.
17. a) U. Schmidt, B. Riedl, G. Haas, H. Griesser, A. Vetter, S. Weinbrenner, Synthesis 1993, 216.
18. b) P. L. Williams, P. Monerris, I. Gonzales, G. Jou, E. Giralt, J. Chem. Soc. Perkin Trans. I 1994, 1969, and references cited therein.
19. Recently published other strategies: a) P. Castejón, A. Morano, M. A. Pericas, A. Riera, Tetrahedron 1996, 52, 7063;
20. b) G. Veeresha, A. Datta, Tetrahedron Lett. 1997, 38, 5223.
21. U. Kazmaier, Angew. Chem. 1994, 106, 1046; Angew. Chem. Int. Ed. Engl. 1994, 33, 998.
22. U. Kazmaier, Angew. Chem. 1994, 106, 1046; Angew. Chem. Int. Ed. Engl. 1994, 33, 998.
23. Review: U. Kazmaier, Liebigs Ann. Chem. / Recueil 1997, 285.
24. U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012. A. Krebs, U. Kazmaier, Tetrahedron Lett. 1996, 37, 7945.
25. U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012. A. Krebs, U. Kazmaier, Tetrahedron Lett. 1996, 37, 7945.
26. U. Kazmaier, A. Krebs, Angew. Chem. 1995, 107, 2213; Angew. Chem. Int. Ed. Engl. 1995, 34, 2012. A. Krebs, U. Kazmaier, Tetrahedron Lett. 1996, 37, 7945.
27. LHMDS is superior to LDA in rearrangements of TFA protected esters, because of less side reactions.
28. 2 can also be applied in most cases.
29. A chiral column (Chira-Si-(L)-Val) was used.
30. a) F. Weygand, E. Frauendorfer, Chem. Ber. 1970, 103, 2437;
31. b) R. J. Bergeron, J. S. McManis, J. Org. Chem. 1988, 53, 3108.
32. H. A. Staab, Liebigs Ann. 1957, 609, 75.
33. 3OD): δ = 175.92, 157.72 (q, J = 31.2 Hz), 115.93 (q, J = 287.6 Hz), 67.61, 56.47, 49.80, 34.11, 26.91, 13.12, 11.27.
34. R. Knorr, A. Trzeciak, W. Bannwarth, D. Gillessen, Tetrahedron Lett. 1989, 30, 1927.
35. 3): δ = 169.47, 158.87, 138.99, 135.54, 128.64, 128.57, 128.44, 116.58, 75.97, 67.04, 58.81, 37.74, 34.53, 16.65.
36. ε.