Synthesis of the indolic pentacyclic core of manadomanzamine A following biogenetically based strategies

European Journal of Organic Chemistry

Volumn , Issue 6, 2012, Pages 1147-1157

  Yan, Lok Hang ^a   Nuhant, Philippe ^b   Sinigaglia, Isabelle ^b   Fromentin, Yann ^a   Marazano, Christian ^b   Delpech, Bernard ^b   Poupon, Erwan ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b CNRS   (France)

Author keywords

Alkaloids; Biomimetic synthesis; Natural products; Polycycles

Indexed keywords

EID: 84857159118     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201101133     Document Type: Article

References (54)

1. J. Peng, K. V. Rao, Y.-M. Choo, M. T. Hamann in Modern Alkaloids, Structure, Isolation, Synthesis and Biology (Eds.:, E. Fattorusso, O. Taglialatela-Scafati), Wiley-VCH, Weinheim, 2008, pp. 189-232.
2. J.-F. Hu, M. T. Hamann, R. Hill, M. Kelly in The Alkaloids, Chemistry and Biology (Ed.:, G. A. Cordell), Academic Press, San Diego, 2003, vol. 60, pp. 207-285.
3. R. Duval, E. Poupon in Biomimetic Organic Synthesis (Eds.:, E. Poupon, B. Nay), Wiley-VCH, Weinheim, 2011, pp. 181-224.
4. J. E. Baldwin, R. C. Whitehead, Tetrahedron Lett. 1992, 33, 2059-2062.
5. J. E. Baldwin, T. D. W. Claridge, A. J. Culshaw, F. A. Heupel, V. Lee, D. R. Spring, R. C. Whitehead, Chem. Eur. J. 1999, 5, 3154-3161.
6. A. Kaiser, X. Billot, A. Gateau-Olesker, C. Marazano, B. C. Das, J. Am. Chem. Soc. 1998, 120, 8026-8034.
7. K. Jakubowicz, K. Ben Abdeljelil, M. Herdemann, M.-T. Martin, A. Gateau-Olesker, A. Al Mourabit, C. Marazano, B. C. Das, J. Org. Chem. 1999, 64, 7381-7387.
8. J.-C. Wypych, T. M. Nguyen, P. Nuhant, M. Bénéchie, C. Marazano, Angew. Chem. 2008, 120, 5498;
9. Angew. Chem. Int. Ed. 2008, 47, 5418-5421.
10. M. Herdemann, A. Al-Mourabit, M.-T. Martin, C. Marazano, J. Org. Chem. 2002, 67, 1890-1897.
11. M. R. Sanchez-Salvatori, C. Marazano, J. Org. Chem. 2003, 68, 8883-8889.
12. I. Sinigaglia, T. M. Nguyen, J.-C. Wypych, B. Delpech, C. Marazano, Chem. Eur. J. 2010, 16, 3594-3597, keramaphidin-type alkaloids
13. J. E. Baldwin, T. D. W. Claridge, F. A. Heupel, R. C. Whitehead, Tetrahedron Lett. 1994, 35, 7829-7832, madangamines
14. H. M. Tong, M.-T. Martin, A. Chiaroni, M. Bénéchie, C. Marazano, Org. Lett. 2005, 7, 2437-2440, sarain A
15. S. Hourcade, A. Ferdenzi, P. Retailleau, S. Mons, C. Marazano, Eur. J. Org. Chem. 2005, 1302-1310.
16. C. S. Ge, S. Hourcade, A. Ferdenzi, A. Chiaroni, S. Mons, B. Delpech, C. Marazano, Eur. J. Org. Chem. 2006, 4106-4114.
17. S. Peixoto, M.-T. Martin, D. Crich, B. Delpech, C. Marazano, Chem. Eur. J. 2011, 17, 9907-9910.
18. xestospongins and related structures:, J. E. Baldwin, A. Melman, V. Lee, C. R. Firkin, R. C. Whitehead, J. Am. Chem. Soc. 1998, 120, 8559-8560.
19. Origin of the pyridine nucleus of haminols (see structure of haminol-1 below):, A. Cutignano, A. Tramice, S. De Caro, G. Villani, G. Cimino, A. Fontana, Angew. Chem. 2003, 115, 2737; Angew. Chem. Int. Ed. 2003, 42, 2633-2636.
20. origin of the side chain:, A. Cutignano, G. Cimino, A. Giordano, G. d′Ippolito, A. Fontana, Tetrahedron Lett. 2004, 45, 2627-2629.
21. J. Peng, J.-F. Hu, A. B. Kazi, Z. Li, M. Avery, O. Péraud, R. T. Hill, S. G. Franzblau, F. Zhang, R. F. Schinazi, S. S. Wirtz, P. Tharnish, M. Kelly, S. Wahyuono, M. T. Hamann, J. Am. Chem. Soc. 2003, 125, 13382-13386.
22. S. M. Allin, L. J. Duffy, J. M. R. Towler, P. C. Bulman Page, M. R. J. Elsegood, B. Saha, Tetrahedron 2009, 65, 10230-10234.
23. see also:, S. M. Allin, L. J. Duffy, P. C. Bulman Page, V. McKee, M. J. McKenzie, Tetrahedron Lett. 2007, 48, 4711-4714.
24. review article:, E. Poupon, E. Gravel, Nat. Prod. Rep. 2010, 27, 32-56.
25. R. Salame, E. Gravel, P. Retailleau, E. Poupon, Org. Biomol. Chem. 2010, 8, 2522-2528.
26. R. Salame, E. Gravel, K. Leblanc, E. Poupon, Org. Lett. 2009, 11, 1891-1894.
27. G. C. Morrison, W. A. Cetenko, J. Shavel Jr., J. Org. Chem. 1967, 32, 2768-2772. However, this skeleton was obtained earlier
28. S. Sugasawa, Y. Deguchi, Chem. Pharm. Bull. 1960, 8, 879-884.
29. P. Nuhant, S. B. Raikar, J.-C. Wypych, B. Delpech, C. Marazano, J. Org. Chem. 2009, 74, 9413-9421.
30. T. M. Nguyen, S. Peixoto, C. Ouairy, T. D. Nguyen, M. Bénéchie, C. Marazano, P. Michel, Synthesis 2010, 103-109.
31. S. S. Malhotra, M. C. Whiting, J. Chem. Soc. 1960, 3812-3822.
32. M. Sheves, N. Friedman, Angew. Chem. 1986, 98, 260;
33. Angew. Chem. Int. Ed. Engl. 1986, 25, 284-286.
34. The conditions for this rearrangement first observed by using a 1-benzyl-5-methyl-2,3-dihydropyridinium salt (K. Ben Abdeljelil, PhD Thesis, Université Paris 11 Orsay, 2000)
35. were improved by addition of water (I. Sinigaglia, PhD Thesis, Université Paris 11 Orsay, 2010).
36. T. Koike, N. Takeuchi, S. Tobinaga, Chem. Pharm. Bull. 1998, 46, 1497-1500.
37. T. Koike, M. Tanabe, N. Takeuchi, S. Tobinaga, Chem. Pharm. Bull. 1997, 45, 243-248.
38. T. Koike, M. Tanabe, N. Takeuchi, S. Tobinaga, Chem. Pharm. Bull. 1997, 45, 27-31.
39. G. Simchen, H. Hoffmann, H. Bredereck, Chem. Ber. 1968, 101, 51-57.
40. D. H. Clemens, W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 2588-2589.
41. H. H. Wasserman, J. L. Yves, J. Org. Chem. 1985, 50, 3573-3580.
42. P. D. Bailey, S. P. Hollinshead, Tetrahedron Lett. 1987, 28, 2879-2882.
43. M. Ohba, I. Natsutani, Tetrahedron 2007, 63, 12689-12694.
44. L. Shen, M. Zhang, Y. Wu, Y. Qin, Angew. Chem. 2008, 120, 3674;
45. Angew. Chem. Int. Ed. 2008, 47, 3618-3621.
46. Structure of compound 45 is reminiscent to that of known marine alkaloids, namely, arborescidines. See for a previous biomimetic synthesis:, B. E. Burm, M. M. Meijler, J. Korver, M. J. Wanner, G.-J. Koomen, Tetrahedron 1998, 54, 6135-6146.
47. A. M. Kearney, C. D. Vanderwal, Angew. Chem. 2006, 118, 7967;
48. Angew. Chem. Int. Ed. 2006, 45, 7803-7806.
49. T. D. Michels, J. U. Rhee, C. D. Vanderwal, Org. Lett. 2008, 10, 4787-4790.
50. S. E. Steinhardt, J. S. Silverston, C. D. Vanderwal, J. Am. Chem. Soc. 2008, 130, 7560-7561.
51. D. B. C. Martin, C. D. Vanderwal, J. Am. Chem. Soc. 2009, 131, 3472-3473.
52. S. E. Steinhardt, C. D. Vanderwal, J. Am. Chem. Soc. 2009, 131, 7546-7547.
53. T. D. Michels, M. J. Kier, A. M. Kearney, C. D. Vanderwal, Org. Lett. 2010, 12, 3093-3095.
54. S. Peixoto, T. M. Nguyen, D. Crich, B. Delpech, C. Marazano, Org. Lett. 2010, 12, 4760-4763.