Studies toward the total synthesis of gambieric acids: Convergent synthesis of the GHIJ-ring fragment having a side chain

Tetrahedron Letters

Volumn 52, Issue 4, 2011, Pages 548-551

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

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Aldol coupling; Gambieric acids; Julia Kocienski reaction; Polycyclic ethers

Indexed keywords

ANTIFUNGAL AGENT; CERIUM; GAMBIERIC ACID DERIVATIVE; NATURAL PRODUCT; POLYETHER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 78650519441     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.127     Document Type: Article

References (54)

1. H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto, and H. Hirota J. Am. Chem. Soc. 114 1992 1102
2. H. Nagai, M. Murata, K. Torigoe, M. Satake, and T. Yasumoto J. Org. Chem. 57 1992 5448
3. A. Morohashi, M. Satake, H. Nagai, Y. Oshima, and T. Yasumoto Tetrahedron 56 2000 8995
4. H. Nagai, Y. Mikami, K. Yazawa, T. Gonoi, and T. Yasumoto J. Antibiot. 46 1993 520
5. B. Sakamoto, H. Nagai, and Y. Hokama Phycologia 35 1996 350
6. M. Inoue, M. Hirama, M. Satake, K. Sugiyama, and T. Yasumoto Toxicon 41 2003 469
7. K. Sato, and M. Sasaki Org. Lett. 7 2005 2441
8. K. Sato, and M. Sasaki Angew. Chem., Int. Ed. 46 2007 2518
9. K. Sato, and M. Sasaki Tetrahedron 63 2007 5977
10. H. Fuwa, A. Suzuki, K. Sato, and M. Sasaki Heterocycles 72 2007 139
11. H. Fuwa, T. Goto, and M. Sasaki Org. Lett. 10 2008 2211
12. H. Fuwa, K. Ishigai, T. Goto, A. Suzuki, and M. Sasaki J. Org. Chem. 74 2009 4024
13. H. Fuwa, S. Noji, and M. Sasaki Chem. Lett. 38 2009 866
14. H. Fuwa, S. Noji, and M. Sasaki J. Org. Chem. 75 2010 5072
15. I. Kadota, N. Oguro, and Y. Yamamoto Tetrahedron Lett. 42 2001 3645
16. I. Kadota, H. Takamura, and Y. Yamamoto Tetrahedron Lett. 42 2001 3649
17. J.S. Clark, T.C. Fessard, and C. Wilson Org. Lett. 6 2004 1773
18. J.S. Clark, M.C. Kimber, J. Robertson, C.S.P. McErlean, and C. Wilson Angew. Chem., Int. Ed. 44 2005 6157
19. S.W. Roberts, and J.D. Rainier Org. Lett. 9 2007 2227
20. T. Saito, and T. Nakata Org. Lett. 11 2009 113
21. P.R. Blakemore, W.J. Cole, P.J. Kocienski, and A. Morley Synlett 1998 26
22. P.R. Blakemore J. Chem. Soc., Perkin Trans. 1 2002 2563
23. C. Assa Eur. J. Org. Chem. 2009 1831
24. K.C. Nicolaou, D.A. Nugiel, E. Couladouros, and C.-K. Hwang Tetrahedron 46 1990 4517
25. A. Fürstner, E. Kattnig, and O. Lepage J. Am. Chem. Soc. 128 2006 9194
26. M. Caron, and K.B. Sharpless J. Org. Chem. 50 1985 1557
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
28. A.N. Rai, and A. Basu Tetrahedron Lett. 44 2003 2267
29. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974
30. Y. Gao, J.M. Klunder, R.M. Hanson, H. Masamune, S.Y. Ko, and K.B. Sharpless J. Am. Chem. Soc. 109 1987 5765
31. P.L. Anelli, C.B. Bifli, F. Montanari, and S. Quici J. Org. Chem. 52 1987 2559
32. K.C. Nicolaou, C.V.C. Prasad, P.K. Somers, and C.-K. Hwang J. Am. Chem. Soc. 111 1989 5330
33. H. Uehara, T. Oishi, M. Inoue, M. Shoji, Y. Nagumo, M. Kosaka, J.-M. Le Brazidec, and M. Hirama Tetrahedron 58 2002 6493
34. H. Fuwa, M. Ebine, A.J. Bourdelais, D.G. Baden, and M. Sasaki J. Am. Chem. Soc. 128 2006 16989
35. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639
36. T. Mukaiyama, and T. Inoue Chem. Lett. 1976 559
37. T. Inoue, and T. Mukaiyama Bull. Chem. Soc. Jpn. 53 1980 174
38. T. Mukaiyama, and J. Matsuo R. Mahrwald, Modern Aldol Reactions Vol. 1 2004 Wiley-VCH Weinheim 127 160
39. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
40. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277
41. S.D. Meyer, and S.L. Schreiber J. Org. Chem. 59 1994 7549
42. For an example, see: K. Kawamura, H. Hinou, G. Matsuo, and T. Nakata Tetrahedron Lett. 44 2003 5259
43. K. Suzuki, and T. Nakata Org. Lett. 4 2002 2739
44. J.L. Luche J. Am. Chem. Soc. 100 1978 2226
45. A.L. Gemal, and J.L. Luche J. Am. Chem. Soc. 103 1981 5454
46. 3SiH and TMSOTf in propionitrile at -78 °C afforded 29 as a single diastereomer in a somewhat lower yield (72%).
47. T.K. Jones, R.A. Reamer, and S.G. Mills J. Am. Chem. Soc. 112 1990 2998
48. For the synthesis of ent-7, see: T. Brandl, and R.W. Hoffmann Eur. J. Org. Chem. 2004 4373
49. Pioneering works on organocerium reagents in organic synthesis, see: T. Imamoto, T. Kusumoto, Y. Tawarayama, Y. Sugiura, T. Mita, Y. Hatanaka, and M. Yokoyama J. Org. Chem. 49 1984 3904
50. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, and Y. Kamiya J. Am. Chem. Soc. 111 1989 4392
51. T. Imamoto Pure Appl. Chem. 62 1990 747
52. For a recent review, see: G. Bartoli, E. Marcantoni, M. Marcolini, and L. Sambri Chem. Rev. 110 2010 6104
53. The Julia-Kocienski reaction of model ketone A and sulfone 7 without cerium chloride resulted in a significant decrease in yield of the trisubstituted alkene products. The scope and limitations of the cerium chloride-mediated Julia-Kocienski reaction will be reported in a full account of this study. Attempted introduction of the side chain to ketone A by other methods, including Wittig and Horner-Wittig olefinations using phosphonium salt B or phosphonate C under various conditions (base: n-BuLi, NaHMDS, or LiHMDS; solvent: THF, DME, or THF/HMPA), proved fruitless and resulted in the recovery of starting material, most probably due to the enolizable nature of A.
54. +] 859.5366, found 859.5388.