Synthesis of (±)-deoxysymbioimine using an intramolecular Diels-Alder reaction with an N-alkoxycarbonyl 2,3-dihydropyridinium cation as the dienophile

Angewandte Chemie - International Edition

Volumn 45, Issue 6, 2006, Pages 932-935

  Snider, Barry B ^a   Che, Qinglin ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Cycloaddition; Diels Alder reaction; Heterocycles; Imines

Indexed keywords

DRUG PRODUCTS; POSITIVE IONS; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLOADDITION; DIELS-ALDER REACTION; HETEROCYCLES; IMINES;

NITROGEN COMPOUNDS;

ALDEHYDE; CATION; DEOXYSYMBIOIMINE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; PYRIDINIUM DERIVATIVE;

ALKYLATION; ANIMAL; ARTICLE; CHEMISTRY; DINOFLAGELLATE; SYNTHESIS;

ALDEHYDES; ALKYLATION; ANIMALS; CATIONS; DINOFLAGELLIDA; HETEROCYCLIC COMPOUNDS, 3-RING; INDICATORS AND REAGENTS; PYRIDINIUM COMPOUNDS;

EID: 32044447258     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503467     Document Type: Article

References (46)

1. a) M. Kita, M. Kondo, T. Koyama, K. Yamada, T. Matsumoto, K.-H. Lee, J.-T. Woo, D. Uemura, J. Am. Chem. Soc. 2004, 126, 4794-4795;
2. b) M. Kita, D. Uemura, Chem. Lett. 2005, 34, 454-459;
3. c) M. Kita, N. Ohishi, K. Washida, M. Kondo, T. Koyama, K. Yamada, D. Uemura, Bioorg. Med. Chem. 2005, 13, 5253-5258.
4. a) J.-L. Gras, J. Org. Chem. 1981, 46, 3738-3741;
5. b) Y. Araki, T. Konoike, J. Org. Chem. 1997, 62, 5299-5309;
6. c) M. Nörret, M. S. Sherburn, Angew. Chem. 2001, 113, 4198-4200;
7. Angew. Chem. Int. Ed. 2001, 40, 4074-4076.
8. D. F. Taber, S. Kong, S. C. Malcolm, J. Org. Chem. 1998, 63, 7953-7956.
9. T. Sammakia, D. M. Johns, G. Kim, M. A. Berliner, J. Am. Chem. Soc. 2005, 127, 6504-6505.
10. a) J. E. Baldwin, D. R. Spring, R. C. Whitehead, Tetrahedron Lett. 1998, 39, 5417-5420;
11. b) 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;
12. c) 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;
13. d) M. Herdemann, A. Al-Mourabit, M.-T. Martin, C. Marazano, J. Org. Chem. 2002, 67, 1890-1897.
14. a) R. F. Francis, C. D. Crews, B. S. Scott, J. Org. Chem. 1978, 43, 3227-3230;
15. b) R. J. Sundberg, D. S. Grierson, H.-P. Husson, J. Org. Chem. 1984, 49, 2400-2404;
16. c) N. Naiman, H. Rollema, E. Johnson, N. Castagnoli, Jr., Chem. Res. Toxicol. 1990, 3, 133-138.
17. a) F. W. Fowler, J. Org. Chem. 1972, 37, 1321-1323;
18. b) S. Raucher, J. E. MacDonald, Synth. Commun. 1980, 10, 325-331;
19. c) R. J. Sundberg, J. D. Bloom, J. Org. Chem. 1981, 46, 4836-4842;
20. d) R. J. Sundberg, G. Hamilton, C. Trindle, J. Org. Chem. 1986, 51, 3672-3679;
21. e) G. Zhao, U. C. Deo, B. Ganem, Org. Lett. 2001, 3, 201-203.
22. a) H. Sonnenschein, T. Kreher, E. Gründemann, R.-P. Krüger, A. Kunath, V. Zabel, J. Org. Chem. 1996, 61, 710-714;
23. b) M. B. Leitner, T. Kreher, H. Sonnenschein, B. Costisella, J. Springer, J. Chem. Soc. Perkin Trans. 2 1997, 377-381.
24. C. H. Heathcock, R. C. D. Brown, T. C. Norman, J. Org. Chem. 1998, 63, 5013-5030.
25. W. Chu, S. Kamitori, M. Shinomiya, R. G. Carlson, F. Takusagawa, J. Am. Chem. Soc. 1994, 116, 2243-2253;
26. 3 in MeOH at reflux for 2 h; see: C. Xie, M. T. C. Runnegar, B. B. Snider, J. Am. Chem. Soc. 2000, 122, 5017-5024.
27. a) R. S. Al-awar, S. P. Joseph, D. L. Comins, J. Org. Chem. 1993, 58, 7732-7739;
28. b) D. L. Comins, R. S. Al-awar, J. Org. Chem. 1995, 60, 711-716.
29. Stereochemical assignments based on coupling constants and NOE interaction studies are presented in detail in the Supporting Information.
30. a) A. P. Kozikowski, P.-u. Park, J. Org. Chem. 1990, 55, 4668-4682;
31. b) D. L. Comins, M. O. Killpack, E. Despagnet, E. Zeller, Heterocycles 2002, 58, 505-519.
32. S. M. Hannick, Y. Kishi, J. Org. Chem. 1983, 48, 3833-3835.
33. M. Kato, V. P. Kamat, A. Yoshikoshi, Synthesis 1988, 699-701.
34. a) P. Krogsgaard-Larsen, K. Thyssen, K. Schaumburg, Acta Chem. Scand. Ser. B 1978, 32, 327-334;
35. b) M. Solymár, A. Liljeblad, L. Lázár, F. Fülöp, L. T. Kanerva, Tetrahedron: Asymmetry 2002, 13, 1923-1928;
36. c) U. Eilitz, F. Lessmann, O. Seidelmann, V. Wendisch, Tetrahedron: Asymmetry 2003, 14, 189-191.
37. a) D. Ma, H. Sun, Org. Lett. 2000, 2, 2503-2505;
38. b) N. Leflemme, P. Dallemagne, S. Rault, Synthesis 2002, 1740-1746;
39. c) D. Ma, Z. Zhu, Tetrahedron Lett. 2003, 44, 8609-8612.
40. J. P. Michael, A. S. Howard, R. B. Katz, M. I. Xwane, Tetrahedron Lett. 1992, 33, 4751-4754.
41. a) D. L. Comins, A. B. Fulp, Tetrahedron Lett. 2001, 42, 6839-6841;
42. b) D. L. Comins, M. J. Sandelier, T. A. Grillo, J. Org. Chem. 2001, 66, 6829-6832.
43. Details of the aldol reaction are provided in the Supporting Information.
44. For similar examples, see: a) C. E. Masse, M. Yang, J. Solomon, J. Panek, J. Am. Chem. Soc. 1998, 120, 4123-4134;
45. b) C. A. Maier, B. Wünsch, Eur. J. Org. Chem. 2003, 714-720.
46. J. R. Beadle, S. H. Korzeniowski, D. E. Rosenberg, B. J. Garcia-Slanga, G. W. Gokel, J. Org. Chem. 1984, 49, 1594-1603.