Synthesis of polypropionate subunits from cyclopropanes

Tetrahedron

Volumn 61, Issue 32, 2005, Pages 7632-7653

  Defosseux, Magali ^a   Blanchard, Nicolas ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

Cyclopropanes; Diastereoselectivity; Electrophilic additions; Mercury; Ring opening

Indexed keywords

PROPIONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ESTERIFICATION; OXYGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 21844468996     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.099     Document Type: Article

References (73)

1. D. O'Hagan The polyketide metabolites 1991 Ellis Horwood New York
2. U. Sankawa D.H.R. Barton K. Nakanishi O. Meth-Cohn Comprehensive natural products chemistry Vol. 1 1999 Elsevier New York
3. M.T. Davies-Coleman, and M.J. Garson Nat. Prod. Rep. 15 1998 477 493
4. T. Henkel, R.M. Brunne, H. Müller, and F. Reichel Angew. Chem., Int. Ed. 38 1999 643 647
5. J. Rohr Angew. Chem., Int. Ed. 39 2000 2847 2849
6. For some examples, see the following articles and references therein: (a) P. Vogel, S. Gerber-Lemaire, A.T. Carmona, K.T. Meilert, and M.-E. Schwenter Pure Appl. Chem. 77 2005 131 137
7. M. Turks, X. Huang, and P. Vogel Chem. Eur. J. 11 2005 465 476
8. L.D. Falder, and E.M. Carreira Org. Lett. 6 2004 2485 2488
9. M. Turks, F. Fonquerne, and P. Vogel Org. Lett. 6 2004 1053 1056
10. M.A. Calter, W. Song, and J. Zhou J. Org. Chem. 69 2004 1270 1275
11. P. Mochirian, B. Cardinal-David, B. Guérin, M. Prévost, and Y. Guindon Tetrahedron Lett. 43 2002 7067 7071
12. B. Breit, and S.K. Zahn J. Org. Chem. 66 2001 4870 4877
13. O. Arjona, R. Menchaca, and J. Plumet J. Org. Chem. 66 2001 2400 2413
14. M.A. Calter, X. Guo, and W. Liao Org. Lett. 3 2001 1499 1501
15. C. Marchionni, and P. Vogel Helv. Chim. Acta 84 2001 431 472
16. J.W. Bode, N. Fraefel, D. Muri, and E.M. Carreira Angew. Chem., Int. Ed. 40 2001 2082 2084
17. I. Paterson, and R. Norcross Chem. Rev. 95 1995 2041 2214
18. R.W. Hoffman Angew. Chem., Int. Ed. Engl. 26 1987 489 503
19. R.W. Hoffman, G. Dakmann, and M.W. Andersen Synthesis 1994 629 638
20. J. Cossy, S. BouzBouz, F. Pradaux, C. Willis, and V. Bellosta Synlett 2002 1595 1606 and references therein
21. D.B. Collum, W.C. Still, and F. Mohamadi J. Am. Chem. Soc. 108 1986 2094 2096
22. A.G.M. Barrett, and W. Tam J. Org. Chem. 62 1997 4653 4664
23. P. Kocovsky, J.M. Grech, and W.L. Mitchell J. Org. Chem. 60 1995 1482 1483
24. P. Kocovsky, J.M. Grech, and W.L. Mitchell Tetrahedron Lett. 37 1996 1125 1128
25. P. Kocovsky, V. Dunn, J.M. Grech, J. Srogl, and W.L. Mitchell Tetrahedron Lett. 37 1996 5585 5588
26. For some applications of the ring-opening of cyclopropanes with mercury(II) salts, see: (a) D.B. Collum, F. Mohamadi, and J.S. Hallock J. Am. Chem. Soc. 105 1983 6882 6889
27. Y. Landais, and L. Parra-Rapado Tetrahedron Lett. 37 1996 1209 1212
28. P. Kocovsky, J. Srogl, M. Pour, and A. Gogoll J. Am. Chem. Soc. 116 1994 186 197
29. P. Kocovsky, and J. Srogl J. Org. Chem. 57 1992 4565 4567
30. P. Kocovsky, V. Dunn, A. Gogoll, and V. Langer J. Org. Chem. 64 1999 101 119
31. U. Mißlitz, H. Primke, and A. de Meijere Chem. Ber. 122 1989 537 543
32. M. Lautens, W. Tam, and J. Blackwell J. Am. Chem. Soc. 119 1997 623 624
33. M. Lautens, and J. Blackwell Synthesis 1998 537 546
34. J. Cossy, N. Blanchard, M. Defosseux, and C. Meyer Angew. Chem., Int. Ed. 41 2002 2144 2146
35. M. Defosseux, N. Blanchard, C. Meyer, and J. Cossy J. Org. Chem. 69 2004 4626 4647
36. For an account concerning the ring-opening of cyclopropylcarbinols with mercury(II) salts, see: C. Meyer, N. Blanchard, M. Defosseux, and J. Cossy Acc. Chem. Res. 36 2003 766 772
37. J. Cossy, N. Blanchard, and C. Meyer Org. Lett. 3 2001 2567 2569
38. J. Cossy, N. Blanchard, C. Hamel, and C. Meyer J. Org. Chem. 64 1999 2608 2609
39. J. Cossy, N. Blanchard, and C. Meyer Synthesis 1999 1063 1075
40. J. Cossy, N. Blanchard, and C. Meyer Eur. J. Org. Chem. 2001 2841 2850
41. J. Cossy, N. Blanchard, and C. Meyer Tetrahedron Lett. 40 1999 8361 8364
42. G.R. De Maré J. Mol. Struct. (Theochem) 153 1987 341 356
43. V.V. Plemenkov, O.J. Butenko, V.V. Zverev, L.V. Ermolaeva, V.M. Vakar, A.V. Ignatchenko, and I.G. Bolesov J. Mol. Struct. 218 1990 195 200
44. D. Arigoni, A. Vasella, K.B. Sharpless, and H.P. Jensen J. Am. Chem. Soc. 95 1973 7917 7919
45. L.M. Stephenson, and D.R. Speth J. Org. Chem. 44 1979 4683 4689
46. J.-L. Luche, L. Rodriguez-Hahn, and P. Crabbé J. Chem. Soc., Chem. Commun. 1978 601 602
47. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639 666
48. A. Mengel, and O. Reiser Chem. Rev. 99 1999 1191 1223
49. W.C. Still, and J. Barrish J. Am. Chem. Soc. 105 1983 2487 2489
50. D.A. Evans, G.C. Fu, and A.H. Hoveyda J. Am. Chem. Soc. 110 1988 6917 6918
51. E.J. Corey, and J.W. Suggs Tetrahedron Lett. 1975 2647 2650
52. G.J. Karabatsos, and N. Hsi J. Am. Chem. Soc. 87 1965 2864 2870
53. M. Pelissier, A. Serafini, J. Devanneaux, J.-F. Labarre, and J.-F. Tocanne Tetrahedron 27 1971 3271 3284
54. G. Descotes, A. Menet, and F. Collonges Tetrahedron 29 1973 2931 2935
55. A.I. Meyers, J.L. Romine, and S.A. Fleming J. Am. Chem. Soc. 110 1988 7245 7247
56. H.N.C. Wong, M.-Y. Hon, C.-H. Tse, Y.-C. Yip, J. Tanko, and T. Hudlicky Chem. Rev. 89 1989 165 198
57. A. De Meiere Angew. Chem., Int. Ed. Engl. 18 1979 809 826
58. M. Lautens, and P.H.M. Delanghe J. Org. Chem. 60 1995 2474 2487
59. S. Ono, S. Shuto, and A. Matsuda Tetrahedron Lett. 37 1996 221 224
60. S. Shuto, S. Ono, Y. Hase, N. Kamiyama, H. Takada, K. Yamasihita, and A. Matsuda J. Org. Chem. 61 1996 915 923
61. G.M. Whitesides, and J. San Fillipo Jr. J. Am. Chem. Soc. 92 1970 6611 6624
62. S.H. Kang, J.H. Lee, and S.B. Lee Tetrahedron Lett. 39 1988 59 62 and references therein
63. D.A. Evans, S.L. Bender, and J. Morris J. Am. Chem. Soc. 110 1988 2506 2526
64. 10 Although, 25″c and 25‴c would have both afforded 26′b after reductive demercuration, it was clearly established by performing the reductive demercuration of the mixture of 25′a and 25″a on large scale that the stereotriad 26′a was the single product generated. Moreover, the relative configuration of compound 26′b was confirmed by a chemical correlation from the known stereotriad 33c.
65. L. Domon, F. Vogeleisen, and D. Uguen Tetrahedron Lett. 37 1996 2773 2776
66. Bicyclic orthoesters can be obtained by condensation of a 1,3,5-triol with an orthoester, see for example: G. Stork, and S.D. Rychnovsky J. Am. Chem. Soc. 109 1987 1565 1567
67. H. Nagaoka, and Y. Kishi Tetrahedron 23 1981 3873 3888
68. C. Gennari, L. Colombo, G. Bertolini, and G. Schimperna J. Org. Chem. 52 1987 2754 2760
69. Y. Yokoyama, Y. Terada, and H. Kawashima Bull. Chem. Soc. Jpn. 64 1991 2563 2565
70. S.D. Rychnovsky, B.N. Rogers, and T.I. Richardson Acc. Chem. Res. 31 1998 9 17
71. I. Paterson, and J.A. Channon Tetrahedron Lett. 33 1992 797 800
72. R.W. Hoffmann Chem. Rev. 89 1989 1841 1860
73. Y. Ohmori, A. Yamashita, R. Tsujita, T. Yamamoto, K. Taniuchi, A. Matsuda, and S. Shuto J. Med. Chem. 46 2003 5326 5333