The asymmetric synthesis of (-)-pumiliotoxin C using tandem catalysis

Tetrahedron

Volumn 60, Issue 43 SPEC. ISS., 2004, Pages 9687-9693

  Dijk, Ewold W ^a   Panella, Lavinia ^a   Pinho, Pedro ^a   Naasz, Robert ^a   Meetsma, Auke ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Alkaloids; Heck allylic substitution; Pumiliotoxin C

Indexed keywords

2 CYCLOHEXENONE; PUMILIOTOXIN; PUMILIOTOXIN C; UNCLASSIFIED DRUG;

ADDITION REACTION; CATALYSIS; CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; TECHNIQUE;

EID: 4544316937     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.148     Document Type: Conference Paper

References (64)

1. J.W. Daly, T. Tokuyama, G. Habermehl, I.L. Karle, and B. Witkop Lieb. Ann. Chem. 729 1969 198
2. For an overview of the natural occurence of pumiliotoxin C and analogues, see (b) T.F. Spande, P. Jain, H.M. Garraffo, L.K. Pannell, H.J.C. Yeh, J.W. Daly, S. Fukumoto, K. Imamura, T. Tokuyama, J.A. Torres, R.R. Snelling, and T.H. Jones J. Nat. Prod. 62 1999 5
3. J.P. Michael Nat. Prod. Rep. 15 1998 595
4. J.W. Daly, Y. Nishizawa, W.L. Padgett, T. Tokuyama, P.J. McCloskey, L. Waykole, A.G. Schulz, and R.S. Aronstam Neurochem. Res. 16 1991 1207
5. A.G. Schulz, A.H. Wang, C. Alva, A. Sebastian, S.D. Glick, D.C. Deecher, and J.M. Bidlack J. Med. Chem. 39 1996 1956
6. For a review of the literature until 1976 see: Y. Inubushi, and T. Ibuka Heterocycles 8 1977 633
7. M. Akashi, Y. Sato, and M. Mori J. Org. Chem. 66 2001 7873
8. A. Padwa, T.M. Heidelbaugh, and J.T. Kuethe J. Org. Chem. 65 2000 2368
9. Y. Shieh, M.P. Yeh, and U.N. Rao J. Chin. Chem. Soc. 47 2000 283
10. T.G. Back, and K. Nakajima Tetrahedron Lett. 38 1997 989
11. J.T. Kuethe, and A. Padwa Tetrahedron Lett. 38 1997 1505
12. G. Mehta, and M. Praveen J. Org. Chem. 60 1995 279
13. A.I. Meyers, and G. Milot J. Am. Chem. Soc. 115 1993 6652
14. K. Paulvannan, and J.R. Stille Tetrahedron Lett. 34 1993 6673
15. R.P. Polniaszek, and L.D. Dillard J. Org. Chem. 57 1992 4103
16. A. Brandi, F.M. Cordero, A. Goti, and A. Guarna Tetrahedron Lett. 33 1992 6697
17. D.L. Comins, and A. Dehghani Tetrahedron Lett. 32 1991 5697
18. N.A. LeBel, and N. Balasubramanian J. Am. Chem. Soc. 111 1989 3363
19. K. Abe, T. Tsugoshi, and N. Nakamura Bull. Chem. Soc. Jpn 57 1984 3351
20. K. Hattori, Y. Matsumura, T. Miyazaki, K. Maruoka, and H. Yamamoto J. Am. Chem. Soc. 103 1981 7368
21. L.E. Overman, and P.J. Jessup J. Am. Chem. Soc. 100 1978 5179
22. T. Ibuka, Y. Mori, and Y. Inubushi Chem. Pharm. Bull. 26 1978 2442
23. W. Oppolzer, C. Fehr, and J. Warneke Helv. Chim. Acta 60 1977 48
24. G. Habermehl, H. Andres, K. Miyahara, B. Witkop, and J.W. Daly Lieb. Ann. Chem. 1976 1577
25. T. Ibuka, Y. Mori, and Y. Inubushi Tetrahedron Lett. 17 1976 3169
26. W. Oppolzer, W. Fröstl, and H.P. Weber Helv. Chim. Acta 58 1975 593
27. G. Habermehl, H. Andres, and B. Witkop Naturwissenschaften 62 1975 345
28. T. Ibuka, N. Masaki, I. Saji, K. Tanaka, and Y. Inubushi Chem. Pharm. Bull. 23 1975 2779
29. T. Ibuka, Y. Inubushi, I. Saji, K. Tanaka, and N. Masaki Tetrahedron Lett. 16 1975 323
30. W. Oppolzer, E. Flaskamp, and L.W. Bieber Helv. Chim. Acta 84 2001 141 145
31. T.G. Back, and K. Nakajima J. Org. Chem. 63 1998 6566
32. T. Riechers, H.C. Krebs, R. Wartchow, and G. Habermehl Eur. J. Org. Chem. 1998 2641
33. M. Naruse, S. Aoyagi, and C. Kibayashi J. Chem. Soc., Perkin Trans. 1 1996 1113
34. S.G. Davies, and G. Bhalay Tetrahedron: Asymmetry 7 1996 1595
35. M. Naruse, S. Aoyagi, and C. Kibayashi Tetrahedron Lett. 35 1994 9213
36. D.L. Comins, and A. Dehghani J. Chem. Soc., Chem. Commun. 1993 1838
37. S. Murahashi, S. Sasao, E. Saito, and T. Naota Tetrahedron 49 1993 8805
38. S. Murahashi, S. Sasao, E. Saito, and T. Naota J. Org. Chem. 57 1992 2521
39. M. Bonin, J. Royer, D.S. Grierson, and H.-P. Husson Tetrahedron Lett. 27 1986 1569
40. K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, and H. Yamamoto J. Am. Chem. Soc. 105 1983 2831
41. W. Oppolzer, and E. Flaskamp Helv. Chim. Acta 60 1977 204
42. M. Toyota, T. Asoh, and K. Fukumoto Heterocycles 45 1997 147
43. M. Toyota, T. Asoh, M. Matsumura, and K. Fukumoto J. Org. Chem. 61 1996 8687
44. M. Toyota, T. Asoh, and K. Fukumoto Tetrahedron Lett. 37 1996 4401
45. A.G. Schultz, P.J. McCloskey, and J.J. Court J. Am. Chem. Soc. 109 1987 6493
46. S. Masamune, L.A. Reed III, J.T. Davis, and W. Choy J. Org. Chem. 48 1983 4441
47. D.L. Comins, and A. Dehghani J. Chem. Soc., Chem. Commun. 1993 1838
48. K.C. Nicolaou, and E.J. Sorensen Classics in Total Synthesis 1996 VCH Weinheim
49. L.F. Tietze Chem. Rev. 96 1996 115
50. B.L. Feringa, M. Pineschi, L.A. Arnold, R. Imbos, and A.H.M. De Vries Angew. Chem., Int. Ed. Engl. 36 1997 2621
51. B.L. Feringa Acc. Chem. Res. 33 2000 346
52. R. Naasz, L.A. Arnold, A.J. Minnaard, and B.L. Feringa Chem. Commun. 2001 735
53. M.L. Moore Org. React. 5 1949 301
54. D.L. Hughes Org. React. 42 1992 335
55. Prepared from formic acid and tosyl isocyanide, see K.S. Feldman, M.M. Bruendl, K. Schildknegt, and A.C. Bohnstedt J. Org. Chem. 61 1996 5440
56. J.R. Henry, L.R. Marcin, M.C. McIntosh, P.M. Scola, G.D. Harris, and S.B. Weinreb Tetrahedron Lett. 30 1989 5709
57. Data have been deposited at the CCDC Nr. 234521.
58. R.C. Larock, and C. Tu Tetrahedron 51 1995 6635 and references cited therein
59. R.C. Larock, Y. Yang, S.M. Weinreb, and R.J. Herr J. Org. Chem. 59 1994 4172
60. P. Pinho, A.J. Minnaard, and B.L. Feringa Org. Lett. 5 2003 259
61. B.A. Patel, and R.F. Heck J. Org. Chem. 43 1978 3898
62. R.F. Heck Org. React. 27 1982 345
63. Ref. 4d. The compound showed 45-90% correspondence with the mass spectrum of pumiliotoxin C from the NIST Mass Spectral Library (1995). See also Ref. 1b
64. M. Akashi, Y. Sato, and M. Mori J. Org. Chem. 66 2001 7873