A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis

European Journal of Organic Chemistry

Volumn , Issue 19, 2005, Pages 4179-4186

  Allin, Steven M ^a   Thomas, Christopher I ^a   Allard, James E ^a   Doyle, Kevin ^b   Elsegood, Mark R J ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b OSI Pharmaceuticals   (United Kingdom)

Author keywords

Asymmetric synthesis; Heterocycles; Lactams; Natural products

Indexed keywords

EID: 29944432383     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500412     Document Type: Article

References (28)

1. S. F. Martin, K. X. Chen, C. T. Early, Org. Lett. 1999, 1, 79-81.
2. J. Yu, T. Wang, X. Liu, J. Deschamps, J. Flippen-Anderson, X. Liao, J. M. Cook, J. Org. Chem. 2003, 68, 7565-7581.
3. M. Logers, L. E. Overman, G. S. Welmaker, J. Am. Chem. Soc. 1995, 117, 9139-9150.
4. A. Deiters, K. Chen, C. T. Early, S. F. Martin, J. Am. Chem. Soc. 2003, 125, 4541-4550.
5. A. Deiters, S. F. Martin, Org. Lett. 2002, 4, 3243-3245.
6. R. S. Fornicola, K. Subburaj, J. Montgomery, Org. Lett. 2002, 4, 615-617.
7. X. Liu, T. Wang, Q. Xu, C. Ma, J. M. Cook, Tetrahedron Lett. 2000, 41, 6299-6303.
8. a) S. M. Allin, C. I. Thomas, J. E. Allard, M. Duncton, M. R. J. Elsegood, M. Edgar, Tetrahedron Lett. 2003, 44, 2335-2337;
9. b) S. M. Allin, D. G. Vaidya, S. L. James, J. E. Allard, T. A. D. Smith, V. McKee, W. P. Martin, Tetrahedron Lett. 2002, 43, 3661-3663;
10. c) S. M. Allin, S. L. James, W. P. Martin, T. A. D. Smith, M. R. J. Elsegood, J. Chem. Soc., Perkin Trans. 1 2001, 3029-3036;
11. d) S. M. Allin, S. L. James, W. P. Martin, T. A. D. Smith, Tetrahedron Lett. 2001, 42, 3943-3946;
12. e) S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1998, 39, 4905-4908.
13. See: S. M. Allin, C. I. Thomas, J. E. Allard, M. Duncton, M. R. J. Elsegood, M. Edgar, Tetrahedron Lett. 2004, 45, 7103-7105;
14. CCDC-227217 for structures 5a (R = 0.072) and CCDC-227218 for structure 6 (R = 0.031) 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.
15. M. Amat, J. Bosch, J. Hidalgo, M. Canto, M. Perez, N. Llor, E. Molins, C. Miravitlles, M. Orozco, J. Luque, J. Org. Chem. 2000, 65, 3074-3084.
16. H. Akimoto, K. Okamura, M. Yui, T. Shioiri, M. Kuramoto, Y. Kikugawa, S. Yamada, Chem. Pharm. Bull. 1974, 22, 2614-2623.
17. [13a];
18. 20 = -84 (c = 1, MeOH).
19. a) A. I. Meyers, T. Sohda, M. F. Loewe, J. Org. Chem. 1986, 51, 3108-3112;
20. b) T. Itoh, Y. Matsuya, Y. Enomoto, A. Ohsawa, Heterocycles 2001, 55, 1165-1171;
21. c) L. Calabi, B. Danieli, G. Lesma, G. Palmisana, Tetrahedron Lett. 1982, 23, 2139-2142;
22. d) L. E. Overman, T. C. Malone, J. Org. Chem. 1982, 47, 5297-5300;
23. e) D. Thielke, J. Wegener, E. Winterfeldt, Chem. Ber. 1975, 108, 1791-1802;
24. f) N. Sydorenko, C. A. Zificsak, A. I. Gerasyuto, R. P. Hsung, Org. Biomol. Chem. 2005, 3, 2140-2144.
25. [17] Compound 12 was ultimately converted to target 14, for which structural confirmation was obtained by X-ray crystallography, thus confirming the E stereochemistry of both the final product and its precursors.
26. S. Routier, L. Sauge, N. Ayerbe, G. Coudert, J.-Y. Merour, Tetrahedron Lett. 2002, 43, 589-591.
27. S. F. Martin, K. X. Chen, C. T. Early, Org. Lett. 1999, 1, 79-81.
28. B. J. Banks, M. J. Calverley, P. D. Edwards, J. Harley-Mason, Tetrahedron Lett. 1981, 22, 1631-1634.