Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: Convergent synthesis of a fully elaborated GHIJ-ring fragment

Tetrahedron

Volumn 67, Issue 35, 2011, Pages 6600-6615

  Tsubone, Koichi ^a   Hashizume, Keisuke ^a   Fuwa, Haruhiko ^a   Sasaki, Makoto ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Convergent synthesis; Gambieric acids; Julia Kocienski olefination; Polycyclic ethers

Indexed keywords

ANTIFUNGAL AGENT; GAMBIERIC ACID; POLYETHER; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CYCLODEHYDRATION; DRUG STRUCTURE; DRUG SYNTHESIS; ETHERIFICATION; JULIA KOCIENSKI OLEFINATION; OLEFINATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 79960949651     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.05.082     Document Type: Article

References (76)

1. H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto, and H. Hirota J. Am. Chem. Soc. 114 1992 1102 1103
2. H. Nagai, M. Murata, K. Torigoe, M. Satake, and T. Yasumoto J. Org. Chem. 57 1992 5448 5453
3. A. Morohashi, M. Satake, H. Nagai, Y. Oshima, and T. Yasumoto Tetrahedron 56 2000 8995 9001
4. H. Fuwa, T. Goto, and M. Sasaki Org. Lett. 10 2008 2211 2214
5. H. Fuwa, K. Ishigai, T. Goto, A. Suzuki, and M. Sasaki J. Org. Chem. 74 2009 4024 4040
6. H. Nagai, Y. Mikami, K. Yazawa, T. Gonoi, and T. Yasumoto J. Antibiot. 46 1993 520 522
7. M. Inoue, M. Hirama, M. Satake, K. Sugiyama, and T. Yasumoto Toxicon 41 2003 469 474
8. B. Sakamoto, H. Nagai, and Y. Hokama Phycologia 35 1996 350 353
9. I. Kadota, N. Oguro, and Y. Yamamoto Tetrahedron Lett. 42 2001 3645 3647
10. I. Kadota, H. Takamura, and Y. Yamamoto Tetrahedron Lett. 42 2001 3649 3651
11. J.S. Clark, T.C. Fessard, and C. Wilson Org. Lett. 6 2004 1773 1776
12. J.S. Clark, M.C. Kimber, J. Robertson, C.S.P. McErlean, and C. Wilson Angew. Chem., Int. Ed. 44 2005 6157 6162
13. K. Sato, and M. Sasaki Org. Lett. 7 2005 2441 2444
14. K. Sato, and M. Sasaki Angew. Chem., Int. Ed. 46 2007 2518 2522
15. K. Sato, and M. Sasaki Tetrahedron 63 2007 5977 6003
16. H. Fuwa, A. Suzuki, K. Sato, and M. Sasaki Heterocycles 72 2007 139 144
17. H. Fuwa, S. Noji, and M. Sasaki Chem. Lett. 38 2009 866 867
18. H. Fuwa, S. Noji, and M. Sasaki J. Org. Chem. 75 2010 5072 5082
19. S.W. Roberts, and J.D. Rainier Org. Lett. 9 2007 2227 2230
20. T. Saito, and T. Nakata Org. Lett. 11 2009 113 116
21. For a preliminary communication see: K. Tsubone, K. Hashizume, H. Fuwa, and M. Sasaki Tetrahedron Lett. 52 2011 548 551
22. K. Suzuki, and T. Nakata Org. Lett. 4 2002 2739 2741
23. For a related example see: K. Kawamura, H. Hinou, G. Matsuo, and T. Nakata Tetrahedron Lett. 44 2003 5259 5261
24. K.C. Nicolaou, D.A. Nugiel, E. Couladouros, and C.-K. Hwang Tetrahedron 46 1990 4517 4552
25. A. Fürstner, E. Kattnig, and O. Lepage J. Am. Chem. Soc. 128 2006 9194 9204
26. M. Caron, and K.B. Sharpless J. Org. Chem. 50 1985 1557 1560
27. L. Alcaraz, J.J. Harnett, C. Mioskowski, J.P. Martel, T. Le Gall, D.-S. Shin, and J.R. Flack Tetrahedron Lett. 35 1994 5449 5452
28. A.N. Rai, and A. Basu Tetrahedron Lett. 44 2003 2267 2269
29. A.J. Mancuso, S.-L. Huang, and D. Swern J. Org. Chem. 43 1978 2480 2482
30. K. Omura, and D. Swern Tetrahedron 34 1978 1651 1660
31. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974 5976
32. Y. Gao, J.M. Klunder, R.M. Hanson, H. Masamune, S.Y. Ko, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765 5780
33. P.L. Anelli, C.B. Bifli, F. Montanari, and S. Quici J. Org. Chem. 52 1987 2559 2562
34. K.C. Nicolaou, C.V.C. Prasad, P.K. Somers, and C.-K. Hwang J. Am. Chem. Soc. 111 1989 5330 5334
35. H. Uehara, T. Oishi, M. Inoue, M. Shoji, Y. Nagumo, M. Kosaka, J.-M. Le Brazidec, and M. Hirama Tetrahedron 58 2002 6493 6512
36. H. Fuwa, M. Ebine, A.J. Bourdelais, D.G. Baden, and M. Sasaki J. Am. Chem. Soc. 128 2006 16989 16999
37. J.P. Parikh, and W.E. Doering J. Am. Chem. Soc. 84 1967 5505 5507
38. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639 666
39. T. Mukaiyama, K. Narasaka, and K. Banno Chem. Lett. 1973 1011 1014
40. T. Mukaiyama, K. Banno, and K. Narasaka J. Am. Chem. Soc. 96 1974 7503 7509
41. T. Mukaiyama, and J. Matsuo R. Mahrwald, Modern Aldol Reactions Vol. 1 2004 Wiley-VCH Weinheim 127 160
42. T. Mukaiyama Angew. Chem., Int. Ed. 43 2004 5590 5614
43. For an example see: D.A. Evans, L. Kværnø, T.B. Dunn, A. Beauchemin, B. Raymer, J.A. Mulder, E.J. Olhava, M. Juhl, K. Kagechika, and D.A. Favor J. Am. Chem. Soc. 130 2008 16295 16309
44. T. Mukaiyama, and T. Inoue Chem. Lett. 1976 559 562
45. T. Inoue, and T. Mukaiyama Bull. Chem. Soc. Jpn. 53 1980 174 178
46. M. Frigero, and M. Santagostino Tetrahedron Lett. 35 1994 8019 8022
47. S. De Munari, M. Frigero, and M. Santagostino J. Org. Chem. 61 1996 9272 9279
48. R.M. Moriarty, and O. Prakash Org. React. 54 1999 273 418
49. S.D. Meyer, and S.L. Schreiber J. Org. Chem. 59 1994 7549 7552
50. J.L. Hubbs, and C.H. Heathcock J. Am. Chem. Soc. 125 2003 12836 12843
51. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155 4156
52. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277 7287
53. J.L. Luche J. Am. Chem. Soc. 100 1978 2226 2227
54. A.L. Gemal, and J.L. Luche J. Am. Chem. Soc. 103 1981 5454 5459
55. M. Sasaki, C. Tsukano, and K. Tachibana Org. Lett. 4 2002 1747 1750
56. C. Tsukano, M. Ebine, and M. Sasaki J. Am. Chem. Soc. 127 2005 4326 4335
57. D.H.R. Barton, and S.W. McCombie J. Chem. Soc., Perkin Trans. 1 1975 1574 1585
58. B.E. Maryanoff, and A.B. Reitz Chem. Rev. 89 1989 863 927
59. K.C. Nicolaou, M.W. Harter, J.L. Gunzner, and A. Nadin Eur. J. Org. Chem. 1997 1283 1301
60. M. Julia, and J.M. Paris Tetrahedron Lett. 1973 4833 4836
61. P.J. Kocienski, B. Lythgoe, and S. Ruston J. Chem. Soc., Perkin Trans. 1 1978 829 834
62. P. Kocienski Phosphorus and Sulfur 24 1985 97 127
63. L.-S. Deng, X.-P. Huang, and G. Zhao J. Org. Chem. 71 2006 4625 4635
64. J.D. White, and M. Kawasaki J. Org. Chem. 57 1992 5292 5300
65. T. Imamoto, T. Kusumoto, Y. Tawarayama, Y. Sugiura, T. Mita, Y. Hatanaka, and M. Yokoyama J. Org. Chem. 49 1984 3904 3912
66. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, and Y. Kamiya J. Am. Chem. Soc. 111 1989 4392 4398
67. T. Imamoto Pure Appl. Chem. 62 1990 747 752
68. G. Bartoli, E. Marcantoni, M. Marcolini, and L. Sambri Chem. Rev. 110 2010 6104 6143
69. For the synthesis of ent-40b see: J. Pospíšil, and I.E. Markó J. Am. Chem. Soc. 129 2007 3516 3517
70. P.R. Blakemore, W.J. Cole, P.J. Kocienski, and A. Morley Synlett 1998 26 28
71. For reviews see: C. Aïssa Eur. J. Org. Chem. 2009 1831 1844
72. P.R. Blakemore J. Chem. Soc., Perkin Trans. 1 2002 2563 2585
73. T.K. Jones, R.A. Reamer, and S.G. Mills J. Am. Chem. Soc. 112 1990 2998 3017
74. For the synthesis of ent-45 see: T. Brandl, and R.W. Hoffmann Eur. J. Org. Chem. 2004 4373 4378
75. O. Mitsunobu Synthesis 1981 1 28
76. K.C.K. Swamy, N.N.B. Kumar, E. Balaraman, and K.V.P.P. Kumar Chem. Rev. 109 2009 2551 2651