Synthesis of the chiral side chain of statins - Lactone versus lactol pathway

European Journal of Organic Chemistry

Volumn , Issue 24, 2006, Pages 5543-5550

  Tararov, Vitali I ^a   Andrushko, Natalia ^a   Andrushko, Vasyl ^a   König, Gerd ^b   Spannenberg, Anke ^a   Börner, Armin ^a,c  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^b ratiopharm GmbH   (Germany)

^c UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Alcohols; Drug design; Lactones; Synthetic methods

Indexed keywords

EID: 33845929620     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600849     Document Type: Article

References (36)

1. E. S. Istvan, J. Deisenhofer, Science 2001, 292, 1160-1164.
2. Contemporary Drug Synthesis (Eds.: J.-J. Li, D. S. Johnson, D. R. Sliskovic, B. D. Roth), Wiley-Interscience, 2004, pp. 113-123.
3. V. I. Tararov, G. König, A. Börner, Adv. Synth. Catal., DOI: 10.1002/adsc.2006291.
4. T. Rosen, M. J. Tashner, C. H. Heathcock, J. Org. Chem. 1984, 49, 3994-4003.
5. a) J. Beecher, I. Brackenridge, S. M. Roberts, J. Tang, A. J. Willetts, J. Chem. Soc., Perkin Trans. 1 1995, 1641-1643;
6. b) J. Tang, I. Brackenridge, S. M. Roberts, J. Beecher, A. J. Willetts, Tetrahedron 1995, 51, 13217-13238.
7. [3] and literature cited therein.
8. S. R. Ghorpade, U. R. Kalkote, S. P. Chavan, S. R. Bhide, T. Ravindranatan, V. G. Puranic, J. Org. Chem. 2001, 66, 6803-6806.
9. F. Bennett, D. W. Knight, G. Fenton, Tetrahedron Lett. 1988, 29, 4865-4868;
10. a) F. Bennett, D. W. Knight, G. Fenton, J. Chem. Soc., Perkin Trans. 1 1991, 133-140.
11. S. J. Maddrell, N. J. Turner, A. Kerridge, A. J. Willetts, J. Crosby, Tetrahedron Lett. 1996, 37, 6001-6004.
12. M. Shimizu, K. Ishii, T. Fujisawa, Chem. Lett. 1997, 765-766.
13. E. Baader, W. Bartmann, G. Beck, A. Bergman, H.-W. Fehlhaber, H. Jendralla, K. Kesseler, R. Saric, H. Schüssler, V. Teetz, M. Weber, G. Wess, Tetrahedron Lett, 1988, 29, 2563-2566.
14. [11]
15. [8]), which is rather difficult to consider to be synthetically valuable for the preparation of statins.
16. E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. J. Am. Chem. Soc 1972, 94, 6190-6191.
17. T. W. Greene, P. G. M. Wuts, Protective groups in Organic Synthesis, Wiley, New York, 1991, p. 80;
18. P. J. Kocienski, "Protecting groups" in The Foundation of Organic Chemistry Series (Eds.: D. Enders, R. Noyori, B. M. Trost), Thieme, Stuttgart, 1994, p. 33.
19. [5]).
20. [4]).
21. a) U. Sunay, B. Fraser-Reid, Tetrahedron Lett. 1986, 27, 5335-5338;
22. b) P. L. Brower, D. E. Butler, C. F. Deering, T. V. Le, A. Millar, T. N. Nanninga, B. D. Roth, Tetrahedron Lett. 1902, 33, 2279-2282.
23. Handbook of Reagents for Organic Synthesis Oxidising and Reducing Agents, (Eds.: S. D. Burke, R. L. Danheiser), John Wiley & Sons, Weinheim, 1999, p. 154.
24. K. E. Pfitzner, J. G. Moffatt, J. Am. Chem. Soc. 1965, 87, 5670.
25. Handbook of Reagents for Organic Synthesis Oxidising and Reducing Agents, (Eds.: S. D. Burke, R. L. Danheiser), John Wiley & Sons, Weinheim, 1999, p. 323.
26. Handbook of Reagents for Organic Synthesis Oxidising and Reducing Agents, (Eds.: S. D. Burke, R. L. Danheiser), John Wiley & Sons, Weinheim, 1999, p. 330.
27. R. Ratliffe, R. Rodehorst, J. Org. Chem. 1970, 35, 4000-4002.
28. P. L. Anelli, F. Montanari, S. Quici, Org. Synth. Coll. Vol. 1993, 8, 367;
29. P. L. Anelli, F. Montanari, S. Quici, Org. Synth. 1990, 69, 212.
30. R. A. Miller, R. S. Hoerrner, Org. Lett. 2003, 5, 285-287.
31. Tararov, A. Korostylev, A. Börner, G. König, P. Bobál', J. Frantisek, G. König, N. Jeker, K. Denike (ratiopharm GmbH), EP 06005510.0 (17.03.2006).
32. H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 1997, 62, 7512-7515.
33. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467.
34. G. M. Sheldrick, SHELXL-93, University of Göttingen, Germany, 1993.
35. Y.-L. Yang, J. R. Falk, Tetrahedron Lett. 1982, 23, 4305-4308.
36. A. P. Kozikowski, C.-S. Li, J. Org. Chem. 1985, 50, 778-785.