Asymmetric synthesis of andavadoic acid via base-catalyzed 5-exo-tet cyclization of a β-hydroperoxy epoxide

Tetrahedron

Volumn 69, Issue 1, 2013, Pages 334-340

  Barnych, Bogdan ^a   Fenet, Bernard ^b   Vatèle, Jean Michel ^a  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

Andavadoic acid; Cyclization; Endoperoxides; Hydroperoxysilylation; Plakortolides

Indexed keywords

ANDAVADOIC ACID; BETA HYDROPEROXY EPOXIDE; EPOXIDE; PEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; PEROXIDATION; PRIORITY JOURNAL;

EID: 84870052961     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.10.022     Document Type: Article

References (54)

1. A.N. Casteel Nat. Prod. Rep. 16 1998 55 73
2. F. Rahm, P.Y. Hayes, and W. Kitching Heterocycles 2004 523 575
3. B.S. Davidson Tetrahedron Lett. 32 1992 7167 7170
4. P.A. Horton, R.E. Longley, M. Kelly-Borges, O.J. McConnell, and L.M. Ballas J. Nat. Prod. 57 1994 1374 1381
5. M. Varoglu, B.M. Peters, and P. Crews J. Nat. Prod. 58 1995 27 36
6. A. Qureshi, J. Salva, M.K. Harper, and D.J. Faulkner J. Nat. Prod. 61 1998 1539 1542
7. D.E. Williams, T.M. Allen, R. Van Soest, H.W. Behrisch, and R.J. Andersen J. Nat. Prod. 64 2001 281 285
8. T.L. Perry, A. Dickerson, A.A. Khan, R.K. Kondru, D.N. Beratan, P. Wipf, M. Kelly, and M.T. Hamann Tetrahedron 57 2001 1483 1487
9. Y. Chen, K.B. Killday, P.J. McCarthy, R. Schemoler, K. Chilson, C. Selitrennikoff, S.A. Pomponi, and A.E. Wright J. Nat. Prod. 64 2001 262 264
10. A. Rudi, R. Afanii, L.G. Gravalos, M. Aknin, E. Gaydou, J. Vacelet, and Y. Kashman J. Nat. Prod. 66 2003 682 685
11. C. Jimenez-Romero, I. Ortiz, J. Vincente, B. Vera, A.D. Rodrigue, S. Nam, and R. Jove J. Nat. Prod. 73 2010 1694 1700
12. K.W.L. Yong, J.J. De Voss, J.N.A. Hooper, and M.J. Garson J. Nat. Prod. 74 2011 194 207
13. K.W.L. Yong, L.K. Lambert, P.Y. Hayes, J.J. De Voss, and M.J. Garson J. Nat. Prod. 75 2012 351 360
14. P. Dai, T.K. Trullinger, X. Liu, and P.H. Dussault J. Org. Chem. 71 2006 2283 2292
15. For a synthesis of another natural product bearing a 3,5-dialkyl-1,2- dioxolane core(plakortide E), see: X.Y. Sun, X.Y. Tian, Z.W. Li, X.S. Peng, and H.N.C. Wong Chem. - Eur. J. 17 2011 5874 5880
16. M. Jung, J. Ham, and J. Song Org. Lett. 4 2002 2763 2765
17. B. Barnych, and J.M. Vatèle Org. Lett. 14 2012 564 567
18. H.D. Doan, J. Gallon, A. Piou, and J.M. Vatèle Synlett 2007 983 985
19. B. Barnych, and J.M. Vatèle Tetrahedron 68 2012 3717 3724
20. B. Barnych, and J.M. Vatèle Synlett 2011 1912 1916
21. For the pioneering work concerning the directing effect of the vinyl group in the endo-cyclization of hydroxyl vinyl epoxides, see: K.C. Nicolaou, C.V.C. Prasad, P.K. Somers, and C.K. Hwang J. Am. Chem. Soc. 111 1989 5330 5334
22. S. Isayama, and T. Mukaiyama Chem. Lett. 1989 573 575
23. S. Isayama Bull. Chem. Soc. Jpn. 63 1990 1305 1310
24. 3SIH peroxidation, see: T. Tokuyasu, S. Kunikawa, K.J. McCullough, A. Masuyama, and M. Nojima J. Org. Chem. 70 2005 251 260
25. G. Görgen, W. Boland, U. Preiss, and H. Simon Helv. Chim. Acta 72 1989 917 928
26. M. Yamaguchi, and I. Hirao Tetrahedron Lett. 24 1983 391 394
27. E.J. Corey, and J. Katzenellenbogen J. Am. Chem. Soc. 91 1969 1851 1852
28. S. Takano, Y. Shimazaki, Y. Sekiguchi, and K. Ogasawara Synthesis 1989 539 541
29. V.K. Yadav, and K.K. Kapoor Tetrahedron 51 1995 8573 8584
30. M.V.R. Reddy, H.C. Brown, and P.V. Ramachandran J. Organomet. Chem. 624 2001 239 243
31. K.B. Sawant, and M.P. Jennings J. Org. Chem. 71 2006 7911 7914
32. J. Ding, and M.P. Jennings J. Org. Chem. 73 2008 5965 5976
33. A. Dossetter, T. Jamison, and E. Jacobsen Angew. Chem.; Int. Ed. 38 1999 2398 2400
34. D. Chavez, and E. Jacobsen Angew. Chem.; Int. Ed. 40 2001 3667 3670
35. D. Chavez, and E. Jacobsen Org. Synth. 82 2005 34 42
36. J. Maddaluno, O. Gaonac'h, Y. Le Gallic, and L. Duhamel Tetrahedron Lett. 36 1995 8591 8594
37. M. Mechelke, J.C. Webb, and J.L. Johnson J. Undergrad. Chem. Res. 4 2005 117 122
38. D.G. Lee, L.N. Congson, U.A. Spitzer, and M.E. Olson Can. J. Chem. 62 1984 1835 1839 and references cited therein
39. L. Lombardo Tetrahedron Lett. 23 1982 4293 4296
40. L. Lombardo Org. Synth. 65 1987 81 89
41. F.N. Tebbe, G.W. Parshall, and G.S. Reddy J. Am. Chem. Soc. 100 1978 3611 3613
42. N.A. Petasis, and E.I. Bzowej J. Am. Chem. Soc. 112 1990 6392 6394
43. W. Tochtermann, S. Bruhn, M. Meints, C. Wolff, E.M. Peters, and H.G. von Schnering Tetrahedron 51 1995 1623 1630
44. S. Matsubara, M. Sugihara, and K. Utimoto Synlett 1998 313 315
45. J. Nebot, P. Romea, and F. Urpi J. Org. Chem. 74 2009 7518 7521
46. P.M. O'Neill, S. Hindley, M.D. Pugh, J. Davies, P.G. Bray, B.K. Park, D.S. Kapu, S.A. Ward, and P.A. Stocks Tetrahedron Lett. 44 2003 8135 8138
47. P. Ghoral, P.H. Dussault, and C. Hu Org. Lett. 10 2008 2401 2404
48. S. Gemma, E. Gabellieri, S.S. Coccone, F. Marti, O. Taglialatela-Scafati, E. Novellino, G. Campiani, and S. Butini J. Org. Chem. 75 2010 2333 2340
49. J.H. Ha, E.Y. Shin, Y. Chung, and J.K. Choi Bull. Korean Chem. Soc. 24 2003 1567 1568
50. D.H.R. Barton, and S.W. McCombie J. Chem. Soc.; Perkin Trans. 1 1975 1574 1585
51. M.J. Robins, and J.S. Wilson J. Am. Chem. Soc. 103 1981 932 933
52. M.J. Robins, J.S. Wilson, and F. Hansske J. Am. Chem. Soc. 105 1983 4059 4065
53. E.J. Corey, S. Kim, S.-E. Yoo, K.C. Nicolaou, L.S. Melvin Jr.; D.J. Brunelle, J.R. Falck, E.J. Trybulski, R. Lett, and P.W. Sheldrake J. Am. Chem. Soc. 100 1978 4620 4622
54. D.A. Evans, T.C. Britton, and J.A. Ellman Tetrahedron Lett. 28 1987 6141 6144