Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: Formal synthesis of (+)-monomorine

Organic Letters

Volumn 11, Issue 9, 2009, Pages 1915-1918

  Paderes, Monissa C ^a   Chemler, Sherry R ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALKENE; AMINE; INDOLIZINE DERIVATIVE; MONOMORINE; OXYGEN; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; ALKENES; AMINES; COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLIZINES; MOLECULAR STRUCTURE; OXYGEN; PYRROLIDINES; STEREOISOMERISM;

EID: 65549154414     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9003492     Document Type: Article

References (52)

1. (a) Lewis, J. R. Nat. Prod. Rep. 2001, 18, 95-128.
2. (b) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446.
3. (a) Nash, R. J.; Fellows, L. E.; Dring, J. V.; Fleet, G. W. J.; Derome, A. E.; Hamor, T. A.; Scofield, A. M.; Watkin, D. J. Tetrahedron Lett. 1988, 29, 2487-2490.
4. (b) Scofield, A. M.; Rossiter, J. T.; Witham, P.; Kite, G. C.; Nash, R. J.; Fellows, L. E. Phytochemistry 1990, 29, 107-109.
5. (a) Kato, A.; Kano, E.; Adachi, I.; Molyneux, R. J.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Wormald, M. R.; Kizu, H.; Ikeda, K.; Asano, N. Tetrahedron: Asymmetry 2003, 14, 325-331.
6. (b) Molyneux, R. J.; Benson, M.; Wong, R. Y.; Tropea, J. E.; Elbein, A. D. J. Nat. Prod. 1988, 51, 1198-1206.
7. (a) Kinzy, T. G.; Harger, J. W.; Carr-Schmid, A.; Kwon, J.; Shastry, M.; Justice, M.; Dinman, J. D. Virology 2002, 300, 60-70.
8. (b) Achenbach, T. V.; Slater, P. E.; Brummerhop, H.; Bach, T.; Muller, R. Antimicrob. Agents Chemother. 2000, 44, 2794-2801.
9. Powell, R. G.; Weisleder, D.; Smith, C. R., Jr.; Rohwedder, W. K. Tetrahedron Lett. 1970, 11, 815-818.
10. Chang, L. C.; Whittaker, N. F.; Bewley, C. A. J. Nat. Prod. 2003, 66, 1490-1494.
11. Warner, G. T.; Perry, C. M. Drugs 2002, 62, 1381-1405.
12. For reviews, see: (a) Wolfe, J. P. Eur. J. Ore. Chem. 2007, 571-582.
13. (b) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213-7256.
14. (c) Coldham, I.; Hufton, R. Chem. Rev. 2005,105, 2765-2810.
15. (d) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 12000, 2862-2891.
16. (e) Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927-964.
17. For intramolecular osmium-catalyzed aminooxygenation reactions, see: (a) Donohoe, T. J.; Churchill, G. H.; Wheelhouse, K. M. P.; Glossop, P. A. Angew. Chem., Int. Ed. 2006, 45, 8025-8028.
18. (b) Donohoe, T. J.; Chughtai, M. J.; Klauber, D. J.; Griffin, D.; Campbell, A. D. J. Am. Chem. Soc. 2006, 128, 2514-2515.
19. (c) Donohoe, T. J.; Bataille, C. J. R.; Gattrell, A.; Kloeges, J.; Rossignol, E. Org. Lett. 2007, 9, 1725-1728.
20. For intramolecular Pd-catalyzed aminooxygenation reactions, see: (a) Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690-7691.
21. (b) Szolcsanyi, P.; Gracza, T. Chem. Commun. 2005, 3948-3950.
22. (c) Desai, L. V.; Sanford, M. S. Angew. Chem., Int. Ed. 2007, 46, 5737-5740.
23. For other intramolecular aminooxygenation reactions, see: (a) Noack, M.; Gottlich, R. Chem. Commun. 2002, 536-537.
24. (b) Chikkana, D.; Han, H. Synlett 2004, 2311-2314.
25. (c) Correa, A.; Tellitu, I.; Dominguez, E.; SanMartin, R. J. Org. Chem. 2006, 71, 8316-8319.
26. (d) Cochran, B. M.; Michael, F. E. Org. Lett. 2008, 10, 5039-5042.
27. (e) Mahoney, J. M.; Smith, C. R.; Johnson, J. N. J. Am. Chem. Soc. 2005, 127, 1354-1355.
28. (f) Fuller, P. H.; Kim, J. W.; Chemler, S. R. J. Am. Chem. Soc. 2008, 130, 17638-17639.
29. (g) Sherman, E. S.; Chemler, S. R. Adv. Synth. Catal. 2009, 351, 467-471.
30. For intermolecular aminohydroxylation of alkenes, see: (a) O'Brien, P. Angew. Chem., Int. Ed. 1999, 38, 326-329.
31. (b) Bolm, C.; Hildebrand, J. P.; Muniz, K. Catalytic Asymmetric Synthesis, 2nd ed; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 412-424.
32. (c) Schlingloff, G.; Sharpless, B. K. Asymmetric Oxidation Reactions; Katsuki, T., Ed.; Oxford University Press: Cambridge, 2001; pp 104-114.
33. (d) Nilov, D.; Rieser, O. Adv. Synth. Catal. 2002, 344, 1169.
34. (e) Bodkin, J. K.; McLeod, M. D. J. Chem. Soc., Perkin Trans. 1 2002, 2733.
35. (f) Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. J. Am. Chem. Soc. 2008,130, 6610-6615.
36. (g) Michaelis, D. J.; Shaffer, C. J.; Yoon, T. P. J. Am. Chem. Soc. 2007, 129, 1866-1867.
37. (h) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179-7181.
38. (i) Michaelis, D. J.; Williamson, K. S.; Yoon, T. P. Tetrahedron 2009, doi:10.1016/j.tet.2009.03.012.
39. (a) Sherman, E. S.; Fuller, P. H.; Kasi, D.; Chemler, S. R. J. Org. Chem. 2007, 72, 3896-3905.
40. (b) Vogler, T.; Studer, A. Synthesis 2008, 1979-1993.
41. (a) Fuller, P. H.; Chemler, S. R. Org. Lett. 2007, 9, 5477-5480.
42. (b) Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079.
43. (c) Baran, P. S.; Richter, P. S. J. Am. Chem. Soc. 2004, 126, 7450-7451.
44. CCDC 696031 (2), 711960 (17), 714177 (20), and 704323 (31) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
45. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353-359.
46. Ritter, F. J.; Rotgans, I. E. M.; Tulman, E.; Verweil, P. E.; Stein, F. Experientia 1973, 29, 530-531.
47. (a) Toyooka, N.; Zhou, D.; Nemoto, H. J. Org. Chem. 2008, 73, 4575-4577, and references therein.
48. (b) Lesma, G.; Colombo, A.; Sacchetti, A.; Silvani, A. J. Org. Chem. 2009, 74, 590-596.
49. (a) Riesinger, S. W.; Löfstedt, J.; Petterson-Fasth, H.; Bäckvall, J. Eur. J. Org. Chem. 1999, 3277-3280.
50. (b) Petterson-Fasth, H.; Riesinger, S. W.; Bäckvall, J. J. Org. Chem. 1995, 60, 6091-6096.
51. Inokuchi, T.; Kawafuchi, H. Tetrahedron 2004, 60, 11969-11975.
52. Evans, P.; McCabe, T.; Morgan, B. S.; Reau, S. Org. Lett. 2005, 7, 43-46.