A short enantioselective synthesis of (+)-L-733,060 via Shi epoxidation of a homoallylic carboxylate

Tetrahedron Letters

Volumn 49, Issue 40, 2008, Pages 5736-5738

  Emmanuvel, Lourdusamy ^a   Sudalai, Arumugam ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

1,2 Aminoalcohols; 3,3 Sigmatropic rearrangement; Asymmetric epoxidation; Lactone

Indexed keywords

3 [3,5 BIS(TRIFLUOROMETHYL)BENZYLOXY] 2 PHENYLPIPERIDINE; CARBOXYLIC ACID DERIVATIVE; DELTA AZIDOLACTONE; LACTONE DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPOXIDATION;

EID: 49549090197     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.086     Document Type: Article

References (34)

1. Baker, R.; Harrison, T.; Hollingworth, G. J.; Swain, C. J.; Williams, B. J. EP 528 495 A1, 1993; Chem. Abstr. 119, 117122h.
2. Harrison T., Williams B.J., Swain C.J., and Ball R.G. Bioorg. Med. Chem. Lett. 4 (1994) 2545
3. Desai M.C., Lefkowitz S.L., Thadeio P.F., Longo K.P., and Snider R.M. J. Med. Chem. 35 (1992) 4911
4. von Euler V.S., and Gaddum J.H. J. Physiol. 72 (1931) 577
5. Chang M.M., and Leeman S.E. J. Biol. Chem. 245 (1970) 4784
6. Pernow B. Pharmacol. Rev. 35 (1983) 85
7. Naanishi S. Physiol. Rev. 67 (1987) 1117
8. Vaughan J. Life Sci. 43 (1988) 1419
9. Lotz M., Vaughan J.H., and Carson D.A. Science 241 (1988) 1218
10. Perianan A., Snyderman R., and Malfroy B. Biochem. Biophys. Res. Commun. 161 (1989) 520
11. Snijdelaar D.G., Dirksen R., Slappendd R., and Crul B.J.P. Eur. J. Pain 4 (2000) 121
12. Datar P., Srivastava S., Coutinho E., and Govil G. Curr. Top. Med. Chem. 4 (2004) 75
13. Lotz M., Vaughan J.H., and Carson D.A. Science 235 (1987) 893
14. Moskowitz M.A. Trends Pharmacol. Sci. 13 (1992) 307
15. Takeuchi Y., Shands E.F.B., Beusen D.D., and Marshall G.R. J. Med. Chem. 41 (1998) 3609
16. Swain C.J. Prog. Med. Chem. 35 (1998) 57
17. Muñoz M., Rosso M., Pérez A., Coveñas R., Rosso R., Zamarriego C., Soult J.A., and Montero I. Invest. Ophthalmol. Vis. Sci. 46 (2005) 2567
18. Miguel M., Marisa R., and Rafael C. Lett. Drug Discov. 3 (2006) 323
19. Takahashi K., Nakano H., and Fujita R. Tetrahedron Lett. 46 (2005) 8927
20. Oshitari T., and Mandai T. Synlett (2006) 3395
21. Yoon Y.-J., Joo J.-E., Lee K.-Y., Kim Y.-H., Oh C.-Y., and Ham W.-H. Tetrahedron Lett. 46 (2005) 739
22. Lee J., Hoang T., Lewis S., Weissman S.A., Askin D., Volante R.P., and Reider P.J. Tetrahedron Lett. 42 (2001) 6223
23. Liu R.H., Fang K., Wang B., Xu M.H., and Lin G.Q. J. Org. Chem. 73 (2008) 3307
24. Cherian S.K., and Kumar P. Tetrahedron: Asymmetry 18 (2007) 982
25. Huang P.Q., Liu L.X., Wei G.B., and Ruan Y.P. Org. Lett. 5 (2003) 1927
26. Bhaskar G., and Rao B.V. Tetrahedron Lett. 44 (2003) 915
27. Davis F.A., and Ramachandar T. Tetrahedron Lett. 49 (2008) 870
28. Johnson W.S., Werthemann L., Bartlett W.R., Brocksom T.J., Li T.-T., Faulkner D.J., and Petersen M.R. J. Am. Chem. Soc. 92 (1970) 741
29. Mori K., Nukada T., and Ebata T. Tetrahedron 37 (1981) 1343
30. Ager D.J., Anderson K., Oblinger E., Shi Y., and VanderRoest J. Org. Process Res. Dev. 11 (2007) 44
31. 3: C, 69.29; H, 8.36; N, 5.05. Found: C, 69.33; H, 8.13; N, 4.92.
32. Schar P., and Renaud P. Org. Lett. 8 (2006) 1569
33. Maio W.A., Sinishtaj S., and Posner G.H. Org. Lett. 9 (2007) 2673
34. Sun H., Abboud K.A., and Horenstein N.A. Tetrahedron 61 (2005) 10462