Improved synthesis of C8-C20 segment of pectenotoxin-2

Tetrahedron Letters

Volumn 52, Issue 43, 2011, Pages 5589-5592

  Fujiwara, Kenshu ^a   Suzuki, Yuki ^a   Koseki, Nao ^a   Murata, Shun Ichi ^a   Murai, Akio ^a   Kawai, Hidetoshi ^a   Suzuki, Takanori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Natural product synthesis; Pectenotoxin 2; Polyether macrolide

Indexed keywords

MALIC ACID; NATURAL PRODUCT; OXYGEN; PECTENOTOXIN 2; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; EPOXIDATION; NONHUMAN; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 80053202165     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.051     Document Type: Article

References (58)

1. T. Yasumoto, M. Murata, Y. Oshima, M. Sano, G.K. Matsumoto, and J. Clardy Tetrahedron 41 1985 1019
2. K. Sasaki, M. Satake, and T. Yasumoto Biosci., Biotechnol., Biochem. 61 1997 1783
3. For a review of non-anomeric spirocyclic acetals: J.E. Aho, P.M. Pihko, and T.K. Rissa Chem. Rev. 105 2005 4406
4. J.H. Jung, C.J. Sim, and C.-O. Lee J. Nat. Prod. 58 1995 1722
5. M. Daiguji, M. Satake, K.J. James, A. Bishop, L. KacKenzie, H. Naoki, and T. Yasumoto Chem. Lett. 27 1998 653
6. Z.-H. Zhou, M. Komiyama, K. Terao, and Y. Shimada Nat. Toxins 2 1994 132
7. M. Hori, Y. Matsuura, R. Yoshimoto, H. Ozaki, T. Yasumoto, and H. Karaki Folia Pharmacol. Jpn. 114 1999 225
8. I. Spector, F. Braet, N. Chochet, and M.R. Bubb Microsc. Res. Tech. 47 1999 18
9. F. Leira, A.G. Cabado, M.R. Vieytes, Y. Roman, A. Alfonso, L.M. Botana, T. Yasumoto, C. Malaguti, and G.P. Rossini Biochem. Pharmacol. 63 2002 1979
10. J.S. Allingham, C.O. Miles, and I. Rayment J. Mol. Biol. 371 2007 959 970
11. B. Espiña, M.C. Louzao, I.R. Ares, E.S. Fonfría, N. Vilariño, M.R. Vieytes, T. Yasumoto, and L.M. Botana Chem. Res. Toxicol. 23 2010 504
12. S. Amano, K. Fujiwara, and A. Murai Synlett 1997 1300
13. D. Awakura, K. Fujiwara, and A. Murai Synlett 2000 1733
14. K. Fujiwara, M. Kobayashi, F. Yamamoto, Y. Aki, M. Kawamura, D. Awakura, S. Amano, A. Okano, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 46 2005 5067
15. K. Fujiwara, Y. Aki, F. Yamamoto, M. Kawamura, M. Kobayashi, A. Okano, D. Awakura, S. Shiga, A. Murai, H. Kawai, and T. Suzuki Tetrahedron Lett. 48 2007 4523
16. Other synthetic studies, see: G.C. Micalizino, and W.R. Roush Org. Lett. 3 2001 1949
17. L.A. Paquette, X. Peng, and D. Bonder Org. Lett. 4 2002 937
18. P.M. Pihko, and J.E. Aho Org. Lett. 6 2004 3849
19. X. Peng, D. Bonder, and L.A. Paquette Tetrahedron 60 2004 9589
20. D. Bonder, J. Liu, T. Muller, and L.A. Paquette Org. Lett. 7 2005 1813
21. R. Halim, M.A. Brimble, and J. Merten Org. Lett. 7 2005 2659
22. R. Halim, M.A. Brimble, and J. Merten Org. Biomol. Chem. 4 2006 1387
23. D. Vellucci, and S.D. Rychnovsky Org. Lett. 9 2007 711
24. S.D. Lotesta, Y. Hou, and L.J. Williams Org. Lett. 9 2007 369
25. P.D. O'Connor, C.K. Knight, D. Friedrich, X. Peng, and L.A. Paquette J. Org. Chem. 72 2007 1747
26. M.A. Brimble, and R. Halim Pure Appl. Chem. 79 2007 153
27. A.M. Heapy, T.W. Wagner, and M.A. Brimble Synlett 2007 2359
28. R.V. Kolakowski, and L.J. Williams Tetrahedron Lett. 48 2007 4761
29. J.E. Aho, E. Salomäki, K. Rissanen, and P.M. Pihko Org. Lett. 10 2008 4179
30. H. Helmboldt, J.E. Aho, and P.M. Pihko Org. Lett. 10 2008 4183
31. S. Carley, and M.A. Brimble Org. Lett. 11 2009 563
32. A.M. Heapy, and M.A. Brimble Tetrahedron 66 2010 5424
33. S. Joyasawal, S.D. Lotesta, N.G. Akhmedov, and L.J. Williams Org. Lett. 12 2010 988
34. G. Vassilikogiannakis, I. Alexopoulou, M. Tofi, and T. Montagnon Chem. Commun. 47 2011 259
35. J.E. Aho, A. Piisola, K.S. Krishnan, and P.M. Pihko Eur. J. Org. Chem. 2011 1682
36. D.P. Canterbury, and G.C. Micalizio Org. Lett. 13 2011 2384
37. A review, see: R. Halim, and M.A. Brimble Org. Biomol. Chem. 4 2006 4048
38. K. Sasaki, J.L.C. Wright, and T. Yasumoto J. Org. Chem. 63 1998 2475
39. D.A. Evans, H.A. Rajapakse, and D. Stenkamp Angew. Chem., Int. Ed. 41 2002 4569
40. D.A. Evans, H.A. Rajapakse, A. Chiu, and D. Stenkamp Angew. Chem., Int. Ed. 41 2002 4573
41. C.-G. Cho, W.-S. Kim, and A.B. Smith III Org. Lett. 7 2005 3569
42. J. Pawlak, K. Nakanishi, T. Iwashita, and E. Borowski J. Org. Chem. 52 1987 2896
43. O. Flögel, M. Ghislaine, O. Amombo, H.-U. Reißig, G. Zahn, I. Brüdgam, and H. Hartl Chem. Eur. J. 9 2003 1405
44. A.J. Mancuso, S.-L. Huang, and D. Swern J. Org. Chem. 43 1978 2480
45. G.A. Kraus, and M.J. Taschner J. Org. Chem. 45 1980 1175
46. G.A. Kraus, and B. Roth J. Org. Chem. 45 1980 4825
47. B.S. Bal, W.E. Childers Jr., and H.W. Pinnick Tetrahedron 37 1981 2091
48. S. Nahm, and S.M. Weinreb Tetrahedron Lett. 22 1981 3815
49. T. Nakata, and T. Oishi Tetrahedron Lett. 21 1980 1641
50. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092
51. B.E. Rossiter, T.R. Verhoeven, and K.B. Sharpless Tetrahedron Lett. 20 1979 4733
52. H. Tomioka, T. Suzuki, H. Nozaki, and K. Oshima Tetrahedron Lett. 23 1982 3387
53. Y. Oikawa, T. Yoshioka, and O. Yonemitsu Tetrahedron Lett. 23 1982 889
54. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
55. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277
56. S. Kobayashi, and T. Mukaiyama Chem. Lett. 3 1974 705
57. T. Katsuki, and K.B. Sharpless J. Am. Chem. Soc. 102 1980 5974
58. D.R. Williams, D.C. Ihle, and S.V. Plummer Org. Lett. 3 2001 1383