Enantioselective total syntheses of nankakurines A and B: Confirmation of structure and establishment of absolute configuration

Journal of the American Chemical Society

Volumn 130, Issue 34, 2008, Pages 11297-11299

  Nilsson, Bradley L ^a,b   Overman, Larry E ^a   De Alaniz, Javier Read ^a   Rohde, Jason M ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF ROCHESTER   (United States)

^c IRONWOOD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; NANKAKURINE A; NANKAKURINE B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; LYCOPODIUM; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 50249109071     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804624u     Document Type: Article

References (49)

1. For reviews of the Lycopodium alkaloids, see: (a) Kobayashi, J.; Morita, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2005; Vol. 61, p 1.
2. (b) Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772.
3. (c) Ayer, W. A.; Trifonov, L. S. In The Alkaloids; Cordell, G. A., Brossi, A., Eds.; Academic Press: New York, 1994; Vol. 45, p 233.
4. (d) Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455-463.
5. (e) MacLean, D. B. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241.
6. (f) MacLean, D. B. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 348.
7. (g) MacLean, D. B. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1968; Vol. 10, p 305.
8. Hirasawa, Y.; Morita, H.; Kobayashi, J. Org. Lett. 2004, 6, 3389-3391.
9. Ayer, W. A.; Ball, L. F.; Browne, L. M.; Tori, M.; Delbaere, L. T. J.; Silverberg, A. Can. J. Chem. 1984, 62, 298-302.
10. Hirasawa, Y.; Kobayashi, J.; Obara, Y.; Nakahata, N.; Kawahara, N.; Goda, Y.; Morita, H. Heterocycles 2006, 68, 2357-2364.
11. (a) Dawbarn, D.; Allen, S. J. Neuropath. Appl. Neurobiol. 2003, 29, 211-230.
12. (b) Dauer, W. Science 2007, 411, 60-62.
13. (a) Hefti, F. Annu. Rev. Pharmacol. Toxicol. 1997, 37, 239-267.
14. (b) Luu, B.; González de Aguilar, J.-L.; Girlanda-Junges, C. Molecules 2000, 5, 1439-1460.
15. (c) Water, S. P.; Tian, Y.; Li, Y.-M.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 13514-13515, and references therein.
16. Kirik, D.; Georgievska, B.; Björklund, A. Nat. Neurosci. 2004, 7, 105-110.
17. (a) For a review, see: Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1007-1046.
18. (b) An intramoleular Mannich reaction was a key element of the first total synthesis of (±)-luciduline; see: Scott, W. L.; Evans, D. A. J. Am. Chem. Soc. 1972, 94, 4779-4780.
19. For examples of carboxylate-terminated aza-Prins biscyclization reactions, see: (a) Heathcock, C. H.; Ruggeri, R. B.; McClure, K. F. J. Org. Chem. 1992, 57, 2585-2594.
20. (b) Lögers, M.; Overman, L. E.; Welmaker, G. S. J. Am. Chem. Soc. 1995, 117, 9139-9150.
21. (a) Oppolzer, W.; Petrzilka, M. J. Am. Chem. Soc. 1976, 98, 6722-6723.
22. (b) Oppolzer, W.; Petrzilka, M. Helv. Chim. Acta 1978, 61, 2755-2762.
23. (a) Luo, F.-T.; Wang, R.-T. Tetrahedron Lett. 1992, 33, 6835-6838.
24. (b) See the Supporting Information for details.
25. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
26. For selected examples of enyne metathesis, see: (a) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2004, 126, 15074-15080.
27. (b) Smulik, J. A.; Diver, S. T. Org. Lett. 2000, 2, 2271-2274.
28. Ipaktschi, J. Chem. Ber. 1984, 117, 856-858.
29. For a recent review, see: (a) Schantl, J. G. Azomethine Imines. In Science of Synthesis; Georg Thieme Verlag: Stuttgart, 2004; Vol. 27, p 731.
30. For select examples, see: (b) Oppolzer, W. Tetrahedron Lett. 1970, 11, 3091-3094.
31. (c) Oppolzer, W. Tetrahedron Lett. 1972, 13, 1707-1710.
32. (d) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10-23.
33. (e) Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Am. Chem. Soc. 1984, 106, 5594-5598.
34. (f) Katz, J. D.; Overman, L. E. Tetrahedron 2004, 60, 9559-9568.
35. (g) Gergely, J.; Morgan, J. B.; Overman, L. E. J. Org. Chem. 2006, 71, 9144-9152.
36. Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2003, 68, 6627-6631.
37. Fleming, I.; Maiti, P.; Ramarao, C. Org. Biomol. Chem. 2003, 1, 3989-4004, and references therein.
38. (a) Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182-2184.
39. (b) Grieco, P. A.; Collins, J. L.; Handy, S. T. Synlett 1995, 1155-1158.
40. (a) Anderson, J. C.; Blake, A. J.; Graham, J. P.; Wilson, C. Org. Biomol. Chem. 2003, 1, 2877-2885.
41. (b) Kim, K. S.; Song, Y. H.; Lee, B. H.; Hahn, C. S. J. Org. Chem. 1986, 51, 404-407.
42. 21
43. Kanemasa, S.; Tomoshige, N.; Wada, E.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 3944-3949.
44. CCDC 690534. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
45. 2 was required to obtain reproducible yields for this reaction; see the Supporting Information for details.
46. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464-1472.
47. To facilitate monitoring reactions and purifying subsequent intermediates, the N-benzyl protecting group was retained until the last step.
48. 4
49. 13C NMR spectra identical to those of the natural products were obtained, consistent with the notion that the natural samples contained an undetermined amount of the conjugate acids. See the Supporting Information for details.