Total synthesis of cryptophycin-24 (arenastatin A) via Prins cyclization

Tetrahedron Letters

Volumn 52, Issue 50, 2011, Pages 6709-6712

  Yadav, J S ^a   Purnima, K V ^a   Subba Reddy, B V ^a   Nagaiah, K ^a   Ghamdi, A K ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Cryptophycins; Cyclic depsipeptides; Grignard reaction; Olefin rearrangement; Prins cyclization

Indexed keywords

ARENASTATIN A;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 80755135454     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.134     Document Type: Article

References (58)

1. R.E. Schwartz, C.F. Hirsch, D.F. Sesin, J.E. Flor, M. Chartrain, R.E. Fromtling, G.H. Harris, M.J. Salvatore, J.M. Liesch, and K. Yudin J. Ind. Microbiol. 5 1990 113 118
2. Hirsch, C. F.; Liesch, J. M.; Salvatore, M. J.; Schwatrz, R. E.; Sesin, D. F. U.S. Patent 4, 946, 835, 1990.
3. G. Trimurtulu, I. Ohtani, G.M.L. Patterson, R.E. Moore, T.H. Corbett, F.A. Valeriote, and L. Demchik J. Am. Chem. Soc. 116 1994 4729 4737
4. C.D. Smith, X. Zhang, S.L. Mooberry, G.M.L. Patterson, and R.E. Moore Cancer Res. 54 1994 3779 3784
5. R.A. Barrow, T. Hemscheidt, J. Liang, S. Paik, R.E. Moore, and M.A. Tius J. Am. Chem. Soc. 117 1995 2479 2490
6. M. Kobayashi, S. Aoki, N. Ohyabu, M. Kurosu, W. Wang, and I. Kitagawa Tetrahedron Lett. 35 1994 7969 7972
7. Y. Koiso, K. Morita, M. Kobayashi, W. Wang, N. Ohyabu, and S. Iwasaki Chem. Biol. Interact. 102 1996 183 191
8. M. Kobayashi, W. Wang, N. Ohyabu, M. Kurosu, and I. Kitagawa Chem. Pharm. Bull. 43 1995 1598 1600
9. G. Trimurtulu, J. Ogino, C.E. Heltzel, T.L. Husebo, C.M. Jensen, L.K. Larsen, G.M.L. Patterson, R.E. Moore, S.L. Mooberry, T.H. Corbett, and F.A. Valeriote J. Am. Chem. Soc. 117 1995 12030 12049
10. M. Kobayashi, W. Wang, N. Ohyabu, M. Kurosu, and I. Kitagawa Chem. Pharm. Bull. 42 1994 2394 2396
11. A.K. Ghosh, and A. Bischoff Org. Lett. 2 2000 1573 1575
12. H.T. Chang, and K.B. Sharpless J. Org. Chem. 61 1996 6456 6457
13. J. Liang, D.W. Hoard, V.V. Khau, M.J. Martinelli, E.D. Moher, R.E. Moore, and M.A. Tius J. Org. Chem. 64 1999 1459 1463
14. D.L. Varie, C. Shih, D.A. Hay, S.L. Andis, T.H. Corbett, L.S. Gossett, S.K. Janisse, M.J. Martinelli, E.D. Moher, R.M. Schultz, and J.E. Toth Bioorg. Med. Chem. Lett. 9 1999 369 374
15. B.H. Norman, T. Hemscheidt, R.M. Schultz, and S.L. Andis J. Org. Chem. 63 1998 5288 5294
16. G.I. Georg, S.M. Ali, V.J. Stella, W.N. Waugh, and R.H. Himes Bioorg. Med. Chem. Lett. 8 1998 1959 1962
17. S. Raghavan, and K.A. Tony J. Org. Chem. 68 2003 5002 5005
18. S. Eißler, A. Stoncius, M. Nahrwold, and N. Sewald Synthesis 22 2006 3747 3789
19. M. Eggen, and G.I. Georg Med. Res. Rev. 22 2002 85 101
20. M.A. Tius Tetrahedron 58 2002 4343 4367
21. N. Kotoku, F. Narumi, T. Kato, M. Yamaguchi, and M. Kobayashi Tetrahedron Lett. 48 2007 7147 7150
22. N. Kotoku, T. Kato, F. Narumi, E. Ohtani, S. Kamada, S. Aoki, N. Okada, S. Nakagawa, and M. Kobayashi Bioorg. Med. Chem. 14 2006 7446 7745
23. J.D. White, J. Hong, and L.A. Robarge Tetrahedron Lett. 39 1998 8779 8782
24. J.D. White, J. Hong, and L.A. Robarge J. Org. Chem. 64 1999 6206 6216
25. M.J. Eggen, C.J. Mossman, S.B. Buck, S.K. Nair, L. Bhat, S.M. Ali, E.A. Reiff, T.C. Boge, and G.I. Georg J. Org. Chem. 65 2000 7792 7799
26. N.K. Tripathy, and G.I. Georg Tetrahedron Lett. 45 2004 5309 5311
27. S. Eißler, T. Bogner, M. Nahrwold, and N. Sewald Chem. Eur. J. 15 2009 11273 11287
28. K.M. Gardinier, and J.W. Leahy J. Org. Chem. 62 1997 7098 7099
29. S.M. Ali, and G.I. Georg Tetrahedron Lett. 38 1997 1703 1706
30. J. Liang, E.D. Moher, R.E. Moore, and D.W. Hoard J. Org. Chem. 65 2000 3143 3147
31. C. Pousst, M. Haddad, and M. Larcheveque Tetrahedron 57 2001 7163 7166
32. L.H. Li, and M.A. Tius Org. Lett. 4 2002 1637 1640
33. C.A. Mast, S. Eißler, A. Stončius, H.G. Stammler, B. Neumann, and N. Sewald Chem. Eur. J. 11 2005 4664 4677
34. S. Eißler, N. Markus, B. Neumann, H.G. Stammler, and N. Sewald Org. Lett. 9 2007 817 819
35. C. Barry, J. St., S.R. Crosby, J.R. Harding, R.A. Hughes, C.D. King, G.D. Parker, and C.L. Willis Org. Lett. 5 2003 2429 2432
36. X.F. Yang, J.T. Mague, and C.J. Li J. Org. Chem. 66 2001 739 747
37. J.S. Yadav, B.V.S. Reddy, K.C. Sekhar, and D. Gunasekar Synthesis 6 2001 885 888
38. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, and N. Niranjan J. Mol. Catal. A: Chem. 210 2004 99 103
39. J.S. Yadav, B.V.S. Reddy, M.S. Reddy, N. Niranjan, and A.R. Prasad Eur. J. Org. Chem. 9 2003 1779 1783
40. D.L. Aubele, S. Wan, and P.E. Floreancig Angew. Chem., Int. Ed. 44 2005 3485 3488
41. C.S. Barry, N. Bushby, J.R. Harding, and C.S. Willis Org. Lett. 7 2005 2683 2686
42. K.N. Cossey, and R.L. Funk J. Am. Chem. Soc. 126 2004 12216 12217
43. S.R. Crosby, J.R. Harding, C.D. King, G.D. Parker, and C.L. Willis Org. Lett. 4 2002 3407 3410
44. S. Marumoto, J.J. Jaber, J.P. Vitale, and S.D. Rychnovsky Org. Lett. 4 2002 3919 3922
45. S.A. Kozmin Org. Lett. 3 2001 755 758
46. J.J. Jaber, K. Mitsui, and S.D. Rychnovsky J. Org. Chem. 66 2001 4679 4686
47. D.J. Kopecky, and S.D. Rychnovsky J. Am. Chem. Soc. 123 2001 8420 8421
48. S.D. Rychnovsky, and C.R. Thomas Org. Lett. 2 2000 1217 1219
49. S.D. Rychnovsky, G. Yang, Y. Hu, and U.R. Khire J. Org. Chem. 62 1997 3022 3023
50. Q. Su, and J.S. Panek J. Am. Chem. Soc. 126 2004 2425 2430
51. J.S. Yadav, M.S. Reddy, P.P. Rao, and A.R. Prasad Tetrahedron Lett. 47 2006 4397 4401
52. J.S. Yadav, M.S. Reddy, and A.R. Prasad Tetrahedron Lett. 47 2006 4937 4941
53. J.S. Yadav, M.S. Reddy, P.P. Rao, and A.R. Prasad Tetrahedron Lett. 47 2006 4995 4998
54. J.S. Yadav, M.S. Reddy, P.P. Rao, and A.R. Prasad Synlett 2007 2049 2052 Refs. cited there in
55. M.E. Furrow, S.E. Schaus, and E.N. Jacobsen J. Org. Chem. 68 1998 6776 6777
56. J.S. Yadav, M.S. Reddy, and A.R. Prasad Tetrahedron Lett. 46 2005 2133 2136
57. H. Fuwa, Y. Okamura, and H. Natsugari Tetrahedron 60 2004 5341 5352
58. J.D. Brabander, and M. Vandewalle Synthesis 8 1994 855 865