An enantioselective approach to the Securinega alkaloids: The total synthesis of (+)-norsecurinine and (+)-allonorsecurinine

Tetrahedron

Volumn 66, Issue 26, 2010, Pages 4701-4709

  Medeiros, Matthew R ^a   Wood, John L ^b  

^a YALE UNIVERSITY   (United States)

^b Department of Ecosystem Science and Sustainability   (United States)

Author keywords

Allonorsecrinine; Claisen rearrangement; Norsecurinine; Rhodium Carbenoid; Securinga Alkaloids; Total Synthesis

Indexed keywords

ALCOHOL; ALKALOID DERIVATIVE; ALLONORSECURININE; ALLYL COMPOUND; CARBENOID; NORSECURININE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CLAISEN REARRANGEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MEDICINAL PLANT; PRIORITY JOURNAL; SECURINEGA; STEREOCHEMISTRY;

SECURINEGA;

EID: 77954243932     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.015     Document Type: Article

References (60)

1. V. Snieckus The Securinega Alkaloids R.H.F. Manske, The Alkaloids Vol. 14 1975 425 506
2. S.M. Weinreb Nat. Prod. Rep. 26 2009 758 775
3. A. Ohsaki, H. Ishiyama, K. Yoneda, and J. Kobayashi Tetrahedron Lett. 44 2003 3097 3099
4. J. Parello Bull. Chim. Soc. Fr. 1968 1117 1129
5. Z. Horii, T. Imanishi, M. Yamauchi, M. Hanaoka, J. Parello, and S. Munavalli Tetrahedron Lett. 13 1972 1877 1880
6. J. Parello, and S. Munavalli C.R. Acad. Sci. Paris 260 1965 337 340
7. P. Petchnaree, N. Bunyapraphatsara, G.A. Cordell, H.J. Cowe, P.J. Cox, R.A. Howie, and S.L. Patt J. Chem. Soc., Perkin Trans. 1 1986 1551 1556
8. L.S. Gan, C.Q. Fan, S.P. Yang, Y. Wu, L.P. Lin, J. Ding, and J.M. Yue Org. Lett. 8 2006 2285 2288
9. T. Nakano, T.H. Yang, and S. Terao Chem. Ind. 1962 1651 1652
10. S. Saito, T. Iwamoto, T. Tanaka, C. Matsumura, N. Sugimoto, Z. Horii, and Y. Tamura Chem. Ind. 1964 1263 1264
11. G.O. Iketubosin, and D.W.M. Mathieson J. Pharm. Pharmacol. 15 1963 810 815
12. R. Alibes, M. Balbe, F. Busque, P. de March, L. Elias, M. Figueredo, and J. Font Org. Lett. 6 2004 1813 1816
13. R. Alibes, P. Bayon, P. de March, M. Figueredo, J. Font, E. Garcia-Garcia, and D. Gonzalez-Galvez Org. Lett. 7 2005 5107 5109
14. G.G. Bardaji, M. Canto, R. Alibes, P. Bayon, F. Busque, P. de March, M. Figueredo, and J. Font J. Org. Chem. 73 2008 7657 7662
15. C.A. Carson, and M.A. Kerr Angew. Chem., Int. Ed. 45 2006 6560 6563
16. B. Dhudshia, B.F.T. Cooper, C.L.B. Macdonald, and A.N. Thadani Chem. Commun. 2009 463 465
17. C.H. Heathcock, and T.W. Vongeldern Heterocycles 25 1987 75 78
18. T. Honda, H. Namiki, M. Kudoh, H. Nagase, and H. Mizutani Heterocycles 59 2003 169 187
19. T. Honda, H. Namiki, M. Kudoh, N. Watanabe, H. Nagase, and H. Mizutani Tetrahedron Lett. 41 2000 5927 5930
20. Z. Horii, M. Hanaoka, T. Imanishi, and C. Iwata Chem. Pharm. Bull. 20 1972 1774 1775
21. Z. Horii, M. Hanaoka, Y. Yamawaki, Y. Tamura, S. Saito, N. Shigematsu, K. Kotera, H. Yoshikawa, Y. Sato, H. Nakai, and N. Sugimoto Tetrahedron 23 1967 1165 1174
22. P.A. Jacobi, C.A. Blum, R.W. Desimone, and U.E.S. Udodong Tetrahedron Lett. 30 1989 7173 7176
23. P. Liu, S. Hong, and S.M. Weinreb J. Am. Chem. Soc. 130 2008 7562 7563
24. P. Magnus, J. Rodriguez-Lopez, K. Mulholland, and I. Matthews Tetrahedron 49 1993 8059 8072
25. S. Saito, H. Yoshikaw, Y. Sato, H. Nakai, N. Sugimoto, Z.I. Horii, M. Hanaoka, and Y. Tamura Chem. Pharm. Bull. 14 1966 313 314
26. D. Gonzalez-Galvez, E. Garcia-Garcia, R. Alibes, P. Bayon, P. de March, M. Figueredo, and J. Font J. Org. Chem. 74 2009 6199 6211
27. G. Han, M.G. LaPorte, J.J. Folmer, K.M. Werner, and S.M. Weinreb J. Org. Chem. 65 2000 6293 6306
28. T. Honda, H. Namiki, K. Kaneda, and H. Mizutani Org. Lett. 6 2004 87 89
29. A.B. Leduc, and M.A. Kerr Angew. Chem. Int. Ed. 47 2008 7945 7948
30. S. Liras, J.E. Davoren, and J. Bordner Org. Lett. 3 2001 703 706
31. As is often the case with discovery in synthesis, this particular transformation was serendipitously observed while attempting something different. Then graduate student Brian Stoltz working with postdoctoral student Hans-Juergen Dietrich was attempting to perform an OH insertion with allylic alcohol substrates. Our interest in the latter was actually stimulated through discussions at Yale Chemistry happy hours with a postdoctoral student from Harry Wasserman's group, Dr. Steve Coats and a good friend of his, Dr. Martin Osterhaut, who was working at Bayer in West Haven, CT. Steve and Martin, who had both spent time in Al Padwa's group, proved to be valuable sources of information regarding rhodium promoted reactions of diazoketones. The chemistry discovered by Stoltz and Dietrich played a central role in four Ph.D. theses from my group (Stoltz, Pflum, Petsch, and Moniz) and clearly continues to occasionally impact our thinking.
32. Stoltz, B.M. Ph.D. Thesis, Yale University, 1997.
33. J.L. Wood, B.M. Stoltz, H.J. Dietrich, D.A. Pflum, and D.T. Petsch J. Am. Chem. Soc. 119 1997 9641 9651
34. B.S. Joshi, D.H. Gawad, S.W. Pelletier, G. Kartha, and K. Bhandary J. Nat. Prod. 49 1986 614 620
35. P. Basabe, O. Bodero, I.S. Marcos, D. Diez, M. De Roman, A. Blanco, and J.G. Urones Tetrahedron 63 2007 11838 11843
36. Y. Kita, J. Sekihachi, Y. Hayashi, Y.Z. Da, M. Yamamoto, and S. Akai J. Org. Chem. 55 1990 1108 1112
37. E. Krawczyk, M. Koprowski, and J. Luczak Tetrahedron: Asymmetry 18 2007 1780 1787
38. R. Peters, C. Diolez, A. Rolland, E. Manginot, and M. Veyrat Heterocycles 72 2007 255 273
39. R. Schobert, and C. Jagusch Synthesis (Stuttg) 2005 2421 2425
40. Klingler, F.D.; Psiorz, M. European Patent 0576888A2, 1993.
41. C.J. Moody, and R.J. Taylor Tetrahedron Lett. 28 1987 5351 5352
42. Moniz, G.A. Ph.D. Thesis, Yale University, 2001.
43. J.L. Wood, and G.A. Moniz Org. Lett. 1 1999 371 374
44. J.L. Wood, G.A. Moniz, D.A. Pflum, B.M. Stoltz, A.A. Holubec, and H.J. Dietrich J. Am. Chem. Soc. 121 1999 1748 1749
45. This observation was made in the original studies of this reaction. See Ref. 16a.
46. Y.G. Gololobov, and L.F. Kasukhin Tetrahedron 48 1992 1353 1406
47. P. Molina, and M.J. Vilaplana Synthesis 1994 1197 1218
48. H. Staudinger, and M. Jules Helv. Chim. Acta 2 1919 635 646
49. H. Staudinger, J. Becker, and H. Hirzel Chem. Ber. 1916 1978 1994
50. H.J. Bestmann, and H. Kolm Chem. Ber. 1963 1948 1958
51. The enantiomeric ratio was determined by chiral HPLC analysis of the benzoate ester of (+)-14 (ChiralPak IC column, 98:2 hexanes/isopropanol).
52. The enantiomeric ratio was determined by chiral HPLC analysis of azide (+)-3 (ChiralPak IC column, 99:1 hexanes/isopropanol). The absolute stereochemistry was initially assigned in accord with observations in previous rhodium-initiated Claisen rearrangements (see Ref. 16b) and is consistent with that expected for the production of (+)-norsecurinine.
53. For the employed IBX protocol, see:
54. J.D. More, and N.S. Finney Org. Lett. 4 2002 3001 3003
55. 4 reductions are subject to solvent effects the reactivity difference displayed by 24 in MeOH versus EtOH was welcome but not anticipated, see: H.C. Brown, S. Narasimhan, and Y.M. Choi J. Org. Chem. 47 1982 4702 4708
56. A similar compound was the sole product observed by Liras and coworkers.
57. H.J. Bestmann Angew. Chem., Int. Ed. 16 1977 349 364
58. R. Schobert Org. Synth. 82 2005 140 146
59. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923 2925
60. C.J. Moody, and R.J. Taylor J. Chem. Soc., Perkin Trans. 1 1989 721 731