Mucohalic acid in Lewis acid catalyzed Mukaiyama aldol reaction: A concise method for highly functionalized γ-substituted γ-butenolides

Tetrahedron Letters

Volumn 46, Issue 12, 2005, Pages 2029-2032

  Angell, Paul ^a   Zhang, Ji ^a   Belmont, Daniel ^a   Curran, Timothy ^a   Davidson, James G ^a  

^a PFIZER INC   (United States)

Author keywords

Butenolides; Lewis acid; Mucohalic acid; Mukaiyama aldol

Indexed keywords

ACETAL DERIVATIVE; ACID; ALDEHYDE; BUTENOLIDE; ETHER DERIVATIVE; LEWIS ACID; MUCOHALIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; MOLECULE; MUKAIYAMA REACTION; SYNTHESIS;

EID: 14644439894     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.147     Document Type: Article

References (50)

1. P.V. Ramachandran, S. Pitre, and H.C. Brown J. Org. Chem. 67 2002 5315
2. B.W. Greatrex, M.C. Kimber, D.K. Taylor, G. Fallon, and E.R.T. Tiekink J. Org. Chem. 67 2002 5307
3. M. Movassaghi, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 2456
4. J. Cossy, C. Rasamison, and D.G. Pardo J. Org. Chem. 66 2001 7195
5. M.-H. Xu, W. Wang, L.-J. Xia, and G.-Q. Lin J. Org. Chem. 66 2001 3953
6. P.V. Ramachandran, H.C. Brown, and S. Pitre Org. Lett. 3 2001 17
7. D. Díaz, and V.S. Martín Org. Lett. 2 2000 335
8. P.V. Ramachandran, M.P. Krzeminski, M.V.R. Reddy, and H.C. Brown Tetrahedron: Asymmetry 10 1999 11
9. B.M. Trost, and Y.H. Rhee J. Am. Chem. Soc. 121 1999 11680
10. E.O. Martins, and J.L. Gleason Org. Lett. 1 1999 1643
11. H.-J. Ha, K.-N. Yoon, S.-Y. Lee, Y.-S. Park, M.-S. Lim, and Y.-G. Yim J. Org. Chem. 63 1998 8062
12. A.-M. Fernandez, J.-C. Plaquevent, and L. Duhamel J. Org. Chem. 62 1997 4007
13. S. Fukuzawa, K. Seki, M. Tatsuzawa, and K. Mutoh J. Am. Chem. Soc. 119 1997 1482
14. A. Vaupel, and P. Knochel J. Org. Chem. 61 1996 5743
15. S.P. Brown, N.C. Goodwin, and D.W.C. MacMillan J. Am. Chem. Soc. 125 2003 1192
16. K. Suzuki, and K. Inomata Tetrahedron Lett. 44 2003 745
17. S. Ma, D. Duan, and Z. Shi Org. Lett. 2 2000 1419
18. S. Ma, and S. Wu J. Org. Chem. 64 1999 9314
19. Y. Nagao, W.-M. Dai, M. Ochiai, and M. Shiro J. Org. Chem. 54 1989 5211
20. C. Böhm, and O. Reiser Org. Lett. 3 2001 1315
21. A. Brecht-Forster, J. Fitremann, and P. Renaud Helv. Chim. Acta 85 2002 3965
22. M. Pohmakotr, W. Harnying, P. Tuchinda, and V. Reutrakul Helv. Chim. Acta 85 2002 3792
23. T.-P. Loh, and P.-L. Lye Tetrahedron Lett. 42 2001 3511
24. S. Drioli, F. Felluga, C. Forzato, P. Nitti, G. Pitacco, and E. Valentin J. Org. Chem. 63 1998 2385
25. H.A. Avedissian, S.C. Sinha, A. Yazbak, A. Sinha, P. Neogi, S.C. Sinha, and E. Keinan J. Org. Chem. 65 2000 6035
26. S.C. Sinha, S.C. Sinha, and E. Keinan J. Org. Chem. 64 1999 7067
27. A. Sinha, S.C. Sinha, S.C. Sinha, and E. Keinan J. Org. Chem. 64 1999 2381
28. J. Zhang, P.G. Blazecka, D. Belmont, and J.G. Davidson Org. Lett. 4 2002 4559
29. W.C. Patt, X.-M. Cheng, J.T. Repine, C. Lee, B.R. Reisdorph, M.A. Massa, A.M. Doherty, K.M. Welch, J.W. Bryant, M.A. Flynn, D.M. Walker, R.L. Schroeder, S.J. Haleen, and J.A. Keiser J. Med. Chem. 42 1999 2162
30. W.C. Patt, J.J. Edmunds, J.T. Repine, K.A. Berryman, B.R. Reisdorph, C. Lee, M.S. Plummer, A. Shahripour, S.J. Haleen, J.A. Keiser, M.A. Flynn, K.M. Welch, E.E. Reynolds, R. Rubin, B. Tobias, H. Hallak, and A.M. Doherty J. Med. Chem. 40 1997 1063
31. P. de March, M. Figueredo, J. Font, and Raya J. Org. Lett. 2 2000 163
32. C. Harcken, and R. Bruckner Angew. Chem., Int. Ed. 36 1997 2750
33. J.-J. Filippi, X. Fernandez, L. Lizzani-Cuvelier, and A.-M. Loiseau Tetrahedron Lett. 43 2002 6267
34. M.-J. Chen, K. Narkunan, and R.-S. Liu J. Org. Chem. 64 1999 8311
35. S. Tsuboi, J. Sakamoto, H. Yamashita, T. Sakai, and M. Utaka J. Org. Chem. 63 1998 1102
36. J. Zhang, P.G. Blazecka, H. Berven, and D. Belmont Tetrahedron Lett. 44 2003 5579
37. E. Beska, and P. Rapos J. Chem. Soc., Perkin Trans. 1 23 1976 2470
38. C.H. Heathcock Comput. Org. Synth. 2 1991 133
39. T. Mukaiyama Org. React. 28 1982 203
40. A. van Oeveren, and B.L. Feringa J. Org. Chem. 61 1996 2920
41. D.A. Evans, M.C. Kozlowski, J.A. Murry, C.S. Burgey, K.R. Campos, B.T. Connell, and R.J. Staples J. Am. Chem. Soc. 121 1999 669
42. F. von der Ohe, and R. Brückner New J. Chem. 24 2000 659
43. The overall desired aldol reaction may be slightly higher-for simplicity of discussion, any remaining uncyclized seco-acid (0-8%) is not reported in Table 1
44. 2 provided nearly quantitative yields of lactone 5a
45. S.K. Bagal, R.M. Adlington, J.E. Baldwin, R. Marquez, and A. Cowley Org. Lett. 5 2003 3049
46. S.K. Bagal, R.M. Adlington, R. Marquez, A.R. Cowley, and J.E. Baldwin Tetrahedron Lett. 44 2003 4993
47. J.D. McCombs, J.W. Blunt, M.V. Chambers, M.H.G. Munro, and W.T. Robinson Tetrahedron 44 1988 1489
48. This result is in agreement with other published work; for example, see: D.A. Evans, C.E. Masse, and J. Wu Org. Lett. 4 2002 3375 and references cited therein
49. Experiments using as low as 5 mol % LA also provided good yield of 5a ; however, the ring-closing event was slower
50. Using a Lewis acid/chiral ligand we have obtained 5d, without purification, in 79% ee; unpublished result