Synthetic study of gymnocin-A: Synthesis of the ABC ring fragment

Tetrahedron Letters

Volumn 55, Issue 48, 2014, Pages 6557-6560

  Sakai, Takeo ^a   Matsushita, Shingo ^a   Arakawa, Shogo ^a   Kawai, Atsuko ^a   Mori, Yuji ^a  

^a MEIJO UNIVERSITY   (Japan)

Author keywords

Convergent synthesis; Gymnocin A; Marine natural product; Oxiranyl anion; Polycyclic ether

Indexed keywords

A ACETOXY ACETAL; ACRYLIC ACID DERIVATIVE; ANION; ETHER DERIVATIVE; GYMNOCIN A; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; DIHYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ETHERIFICATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; WILLIAMSON REACTION;

EID: 84910144911     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.10.014     Document Type: Article

References (48)

1. J.-M. Kornprobst Encyclopedia of Marine Natural Products Vols. 1-3 2010 Wiley-Blackwell Weinhein, Germany
2. Y. Shimizu Dinoflagellate Toxins P.J. Scheuer, Marine Natural Products Vol. 1 1978 Academic Press New York
3. Y. Shimizu Chem. Rev. 93 1993 1685 1698
4. T. Yasumoto, and M. Murata Chem. Rev. 93 1993 1897 1909
5. M. Murata, and T. Yasumoto Nat. Prod. Rep. 17 2000 293 314
6. T. Yasumoto Chem. Rec. 1 2001 228 242
7. A.H. Daranas, M. Norte, and J.J. Fernández Toxicon 39 2001 1101 1132
8. K.A. Steidinger, J.H. Landsberg, L.J. Flewelling, and B.A. Kirkpatrick Toxic Dinoflagellates P.J. Walsh, S.L. Smith, L.E. Fleming, H.M. Solo-Gabriele, W.H. Gerwick, Ocean and Human Health: Risks and Remedies from the Sea 2008 Academic Press Burlington, MA, USA 239 256 Chapter 13
9. M. Satake, M. Shoji, Y. Oshima, H. Naoki, T. Fujita, and T. Yasumoto Tetrahedron Lett. 43 2002 5829 5832
10. Y. Hamamoto, K. Tachibana, P.T. Holland, F. Shi, V. Beuzenberg, Y. Itoh, and M. Satake J. Am. Chem. Soc. 134 2012 4963 4968
11. M. Satake, Y. Tanaka, Y. Ishikura, Y. Oshima, H. Naoki, and T. Yasumoto Tetrahedron Lett. 46 2005 3537 3540
12. For total synthesis reviews, see: M. Inoue Chem. Rev. 105 2005 4379 4405
13. T. Nakata Chem. Rev. 105 2005 4314 4347
14. K.C. Nicolaou, M.O. Frederick, and R.J. Aversa Angew. Chem., Int. Ed. 47 2008 7182 7225
15. M. Sasaki, and H. Fuwa Nat. Prod. Rep. 25 2008 401 426
16. M. Isobe, and A. Hamajima Nat. Prod. Rep. 27 2010 1204 1226
17. For recent total synthesis, see: M. Ebine, H. Fuwa, and M. Sasaki Org. Lett. 10 2008 2275 2278
18. M.T. Crimmins, J.L. Zuccarello, J.M. Ellis, P.J. McDougall, P.A. Haile, J.D. Parrish, and K.A. Emmitte Org. Lett. 11 2009 489 492
19. H. Takamura, S. Kikuchi, Y. Nakamura, Y. Yamagami, T. Kishi, I. Kadota, and Y. Yamamoto Org. Lett. 11 2009 2531 2534
20. H. Furuta, Y. Hasegawa, and Y. Mori Org. Lett. 11 2009 4382 4385
21. Y. Zhang, J. Rohanna, J. Zhou, K. Iyer, and J.D. Rainier J. Am. Chem. Soc. 133 2011 3208 3216
22. S. Yamashita, Y. Ishihara, H. Morita, J. Uchiyama, K. Takeuchi, M. Inoue, and M. Hirama J. Nat. Prod. 74 2011 357 364
23. T. Kuranaga, N. Ohtani, R. Tsutsumi, D.G. Baden, J.L.C. Wright, M. Satake, and K. Tachibana Org. Lett. 13 2011 696 699
24. H. Fuwa, K. Ishigai, K. Hashizume, and M. Sasaki J. Am. Chem. Soc. 134 2012 11984 11987
25. K. Ishigai, H. Fuwa, K. Hashizume, R. Fukazawa, Y. Cho, M. Yotsu-Yamashita, and M. Sasaki Chem.-Eur. J. 19 2013 5276 5288
26. C. Tsukano, and M. Sasaki J. Am. Chem. Soc. 125 2003 14294 14295
27. C. Tsukano, M. Ebine, and M. Sasaki J. Am. Chem. Soc. 127 2005 4326 4335
28. C. Tsukano, and M. Sasaki Tetrahedron Lett. 47 2006 6803 6807
29. A.R. Van Dyke, and T.F. Jamison Angew. Chem., Int. Ed. 48 2009 4430 4432
30. T. Sakai, A. Sugimoto, and Y. Mori Org. Lett. 13 2011 5850 5853
31. T. Sakai, A. Sugimoto, H. Tatematsu, and Y. Mori J. Org. Chem. 77 2012 11177 11191
32. T. Sakai, H. Asano, K. Furukawa, R. Oshima, and Y. Mori Org. Lett. 16 2014 2268 2271
33. Y. Mori, and H. Hayashi J. Org. Chem. 66 2001 8666 8668
34. Y. Mori, K. Nogami, H. Hayashi, and R. Noyori J. Org. Chem. 68 2003 9050 9060
35. E. Lee, J.S. Tae, C. Lee, and C.M. Park Tetrahedron Lett. 34 1993 4831 4834
36. Y. Yuasa, W. Sato, and S. Shibuya Synth. Commun. 27 1997 573 585
37. E. Lee, H.Y. Song, and H.J. Kim J. Chem. Soc., Perkin Trans. 1 1999 3395 3396
38. E.J. Jeong, E.J. Kang, L.T. Sung, S.K. Hong, and E. Lee J. Am. Chem. Soc. 124 2002 14655 14662
39. M.R. Dyson, P.L. Coe, and R.T. Walker Carbohydr. Res. 216 1991 237 248
40. M.A. Blanchette, W. Choy, J.T. Davis, A.P. Essenfeld, S. Masamune, W.R. Roush, and T. Sakai Tetrahedron Lett. 25 1984 2183 2186
41. N. Hashimoto, T. Aoyama, and T. Shioiri Tetrahedron Lett. 21 1980 4619 4622
42. N. Hashimoto, T. Aoyama, and T. Shioiri Chem. Pharm. Bull. 30 1982 119 124
43. Y. Mori, K. Yaegashi, and H. Furukawa Tetrahedron 53 1997 12917 12932
44. T. Sakai, S. Ito, H. Furuta, Y. Kawahara, and Y. Mori Org. Lett. 14 2012 4564 4567
45. H. Liu, C. Sun, N.-K. Lee, R.F. Henry, and D. Lee Chem.-Eur. J. 18 2012 11889 11893
46. K. Fujiwara, D. Takaoka, K. Kusumi, K. Kawai, and A. Murai Synlett 2001 691 693
47. K. Fujiwara, Y. Koyama, K. Kawai, H. Tanaka, and A. Murai Synlett 2002 1835 1838
48. K. Fujiwara, D. Sato, M. Watanabe, H. Morishita, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 45 2004 5243 5246