A unified strategy for the synthesis of 7-membered-ring-containing Lycopodium alkaloids

Journal of the American Chemical Society

Volumn 136, Issue 38, 2014, Pages 13442-13452

  Lee, Amy S ^a   Liau, Brian B ^a   Shair, Matthew D ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETICS; BIOSYNTHESIS;

BIOSYNTHETIC PRECURSORS; CASCADE REACTIONS; DIASTEREOSELECTIVE; MANNICH REACTIONS; NATURAL PRODUCTS; STRUCTURAL RELATIONSHIP; SYNTHETIC STRATEGIES; TOTAL SYNTHESIS;

ALKALOIDS;

ALKALOID; DEHYDROLYCOPECURINE; FASTIGIATINE; HIMERADINE A; IMINE; LYCONADIN A; LYCONADIN B; LYCOPECURINE; UNCLASSIFIED DRUG; FUSED HETEROCYCLIC RINGS; POLYCYCLIC HYDROCARBON; QUINOLIZINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; LYCOPODIUM; NUCLEAR OVERHAUSER EFFECT; NUCLEOPHILICITY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKALOIDS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; LYCOPODIUM; MODELS, MOLECULAR; POLYCYCLIC COMPOUNDS; QUINOLIZINES;

EID: 84941028337     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja507740u     Document Type: Article

References (52)

1. Kobayashi, J.; Morita, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2005; Vol. 61, pp 1-57.
2. Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772.
3. Ayer, W. A.; Trifonov, L. S. In The Alkaloids; Cordell, G. A., Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, pp 233-266.
4. Morita, H.; Hirasawa, Y.; Kobayashi, J. J. Org. Chem. 2003, 68, 4563-4566.
5. Gerard, R. V.; MacLean, D. B.; Fagianni, R.; Lock, C. J. Can. J. Chem. 1986, 64, 943-949.
6. Gerard, R. V.; MacLean, D. B. Phytochemistry 1986, 25, 1143-1150.
7. Ayer, W. A.; Altenkirk, B.; Masaki, N.; Valverde-Lopez, S. Can. J. Chem. 1969, 47, 2449-2455.
8. Ayer, W. A.; Masaki, N. Can. J. Chem. 1971, 49, 524-527.
9. Braekman, J. C.; Hootele, C.; Ayer, W. A. Bull. Soc. Chim. Belg. 1971, 80, 83-90.
10. Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. J. Org. Chem. 2001, 66, 5901-5904.
11. Ishiuchi, K.; Kubota, T.; Hoshino, T.; Obara, Y.; Nakahata, N.; Kobayashi, J. Bioorg. Med. Chem. 2006, 14, 5995-6000.
12. Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594-9595.
13. Liau, B. B. Ph.D. Thesis, Harvard University, 2013.
14. Tori, M.; Shimoji, T.; Shimura, E.; Takaoka, S.; Nakashima, K.; Sono, M.; Ayer, W. A. Phytochemistry 2000, 53, 503-509.
15. Beshore, D. C.; Smith, A. B., III. J. Am. Chem. Soc. 2007, 129, 4148-4149.
16. Beshore, D. C.; Smith, A. B., III. J. Am. Chem. Soc. 2008, 130, 13778-13789.
17. Allinger, N. L.; Riew, C. K. Tetrahedron Lett. 1966, 12, 1269-1272.
18. Stork, G.; Kretchmer, R. A.; Schlessinger, R. H. J. Am. Chem. Soc. 1968, 90, 1647-1648.
19. Medda, A. K.; Lee, H.-S. Synlett 2009, 6, 921-924.
20. Nicolaou, K. C.; Hwang, C.-K.; Duggan, M. E.; Nugiel, D. A.; Abe, Y.; Reddy, K. B.; DeFrees, S. A.; Reddy, D. R.; Awartani, R. A.; Conley, S. R.; Rutjes, F. P. J. T.; Theodorakis, E. A. J. Am. Chem. Soc. 1995, 117, 10227-10238.
21. Linghu, X.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2007, 46, 7671-7673.
22. Danishefsky, S. Acc. Chem. Res. 1979, 12, 66-72.
23. Majetich, G.; Leigh, A. J.; Condon, S. Tetrahedron Lett. 1991, 32, 605-608.
24. Knobloch, E.; Brückner, R. Synlett 2008, 12, 1865-1869.
25. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734-736.
26. Johnson, C. D. Acc. Chem. Res. 1993, 26, 476-482.
27. Stafford, J. A.; Brackeen, M. F.; Karanewsky, D. S.; Valvano, N. L. Tetrahedron Lett. 1993, 34, 7873-7876.
28. Lambert, P. H.; Vaultier, M.; Carrié, R. J. Org. Chem. 1985, 50, 5352-5356.
29. Movassaghi, M.; Chen, B. Angew. Chem., Int. Ed. 2007, 46, 565-568.
30. Schumann, D.; Naumann, A. Liebigs Ann. Chem. 1983, 220-225.
31. Gosh, S. K.; Buchanan, G. S.; Long, Q. A.; Wei, Y.; Al-Rashid, Z. F.; Sklenicka, H. M.; Hsung, R. P. Tetrahedron 2008, 64, 883-893.
32. House, H. O.; Tefertiller, B. A.; Olmstead, H. D. J. Org. Chem. 1968, 33, 935-942.
33. Marcoux, D.; Binschädler, P.; Speed, A. W. H.; Chiu, A.; Pero, J. E.; Borg, G. A.; Evans, D. A. Org. Lett. 2011, 13, 3758-3761.
34. Vink, M. K. S.; Schortinghuis, C. A.; Luten, J.; Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. J. Org. Chem. 2002, 67, 7869-7871.
35. Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 935-936.
36. Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734-3735.
37. Beak, P.; Lee, W. K. J. Org. Chem. 1990, 55, 2578-2580.
38. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109-1117.
39. Dieter, R. K.; Oba, G.; Chandupatla, K. R.; Topping, C. M.; Lu, K.; Watson, R. T. J. Org. Chem. 2004, 69, 3076-3086.
40. Guerrero, C. A.; Sorensen, E. J. Org. Lett. 2011, 13, 5164-5167.
41. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
42. Movassaghi, M.; Tjandra, M.; Qi, J. J. Am. Chem. Soc. 2009, 131, 9648-9650.
43. Altman, R. A.; Nilsson, B. L.; Overman, L. E.; Alaniz, J. R.; Rohde, J. M.; Taupin, V. J. Org. Chem. 2010, 75, 7519-7534.
44. Martin, C. L.; Overman, L. E.; Rohde, J. M. J. Am. Chem. Soc. 2008, 130, 7568-7569.
45. Heathcock, C. H.; Kleinman, E.; Binkley, E. S. J. Am. Chem. Soc. 1978, 100, 8036-8037.
46. Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054-1068.
47. Bisai, A.; West, S. W.; Sarpong, R. J. Am. Chem. Soc. 2008, 130, 7222-7223.
48. West, S. P.; Bisai, A.; Lim, A. D.; Narayan, R. R.; Sarpong, R. J. Am. Chem. Soc. 2009, 131, 11187-11194.
49. Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2011, 133, 418-419.
50. Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2013, 135, 3243-3247.
51. Yang, Y.; Haskins, C. W.; Zhang, W.; Low, P. L.; Dai, M. Angew. Chem., Int. Ed. 2014, 53, 3922-3925.
52. Högenauer, K.; Baumann, K.; Mulzer, J. Tetrahedron Lett. 2000, 41, 9229-9232.