Towards a total synthesis of quinocarcin: Diastereoselective synthesis of functionalized azepino[1,2-b]isoquinolines

European Journal of Organic Chemistry

Volumn , Issue 17, 2004, Pages 3611-3622

  Koepler, Oliver ^a   Laschat, Sabine ^b   Baro, Angelika ^b   Fischer, Peter ^b   Miehlich, Burkhard ^b   Hotfilder, Marc ^c   Le Viseur, Christoph ^c  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

^c UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Catalysis; Ene reaction; Lewis acids; Natural products; Nitrogen heterocycles

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOALCOHOL; BENZOTRIAZOLE DERIVATIVE; ESTER; ISOQUINOLINE DERIVATIVE; LEWIS ACID; OXAZOLIDINONE DERIVATIVE; PHENYLALANINE; QUINOCARCIN; TETRAHYDROISOQUINOLINE; TRICYCLIC OXAZOLIDINONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 4544387854     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400231     Document Type: Article

References (56)

1. [1a] J. Sygusch, F. Brisse, S. Hanessian, D. Kluepfel, Tetrahedron Lett. 1974, 4021-4023.
2. [1b] D. Kluepfel, H. A. Baker, G. Piattoni, S. N. Sehgal, A. Sidorowicz, K. Singh, C. Vezina, J. Antibiot. 1975, 28, 497-502.
3. [2a] K. L. Rinehart, T. G. Holt, N. L. Fregeau, P. A. Keifer, G. R. Wilson, T. J. Perun, R. Sakai, A. G. Thompson, J. G. Stroh, L. S. Shield, D. S. Seigier, J. Nat. Prod 1990, 53, 771-792.
4. [2b] K. L. Rinehart, T. G. Holt, N. L. Fregeau, J. G. Stroh, P. A. Keifer, F. Sun, L. H. Li, D. G. Martin, J. Org. Chem. 1990, 55, 4512-4515.
5. [2c] A. E. Wright, D. A. Forleo, G. P. Gunawardana, S. P. Gunasekera, F. E. Koehn, O. J. McConnell, J. Org. Chem. 1990, 55, 4508-4512.
6. [2d] W. Jin, R. M. Williams, Tetrahedron Lett. 2003, 44, 4635-4639.
7. [2e] J. J. N. Veerman, R. S. Bon, B. T. B. Hue, D. Girones, F. P. J. T. Rutjes, J. H. van Maarseveen, H. Hiemstra, J. Org. Chem. 2003, 68, 4486-4494.
8. [2f] B. Herberich, M. Kinugawa, A. Vazquez, R. M. Williams, Tetrahedron Lett. 2001, 42, 543-546.
9. [2g] C. Cuevas, M. Perez, M. J. Martin, J. L. Chicharro, C. Fernandez-Rivas, M. Flores, A. Francesch, P. Gallego, M. Zarzuelo, F. de la Calle, J. Garcia, C. Polanco, I. Rodriguez, I. Manzanares, Org. Lett. 2000, 2, 2545-2548.
10. [2h] E. J. Martinez, E. J. Corey, Org. Lett. 2000, 2, 993-996.
11. [2i] S. Jeedigunta, J. M. Krenisky, R. G. Kerr, Tetrahedron 2000, 56, 3303-3307.
12. [2j] B. Zhou, J. Guo, S. J. Danishefsky, Tetrahedron Lett. 2000, 41, 2043-2046.
13. [2k] B. Zhou, S. Edmondson, J. Padron, S. J. Danishefsky, Tetrahedron Lett. 2000, 41, 2039-2042.
14. [3a] F. Tomita, K. Takahashi, K. Shimizu, J. Antibiot. 1983, 36, 463-467.
15. [3b] K. Takahashi, F. Tomita, J. Antibiot. 1983, 36, 468-470.
16. [3c] B. Herberich, J. D. Scott, R. M. Williams, Bioorg. Med. Chem. 2000, 8, 523-532.
17. [3d] H. He, B. Shen, G. T. Carter, Tetrahedron Lett. 2000, 41, 2067-2071.
18. [4a] M. E. Flanagan, R. M. Williams, J. Org. Chem. 1995, 60, 6791-6797.
19. [4b] T. Fukuyama, J. J. Nunes, J. Am. Chem. Soc. 1988, 110, 5196-5198.
20. [4c] S. J. Danishefsky, P. J. Harrison, R. R. Webb, B. T. O'Neill, J. Am. Chem. Soc. 1985, 107, 1421-1423.
21. [5a] T. Katoh, M. Kirihara, Y. Nagata, Y. Kobayashi, K. Arai, J. Minami, S. Terashima, Tetrahedron 1994, 50, 6239-6258.
22. [5b] P. Garner, W. B. Ho, H. Shin, J. Am. Chem. Soc. 1992, 114, 2767-2768.
23. [6a] S. Laschat, T. Fox, Synthesis 1997, 475-479.
24. [6b] S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838.
25. [6c] S. Laschat, M. Grehl, Angew. Chem. 1994, 106, 475-478; Angew. Chem. Int. Ed. Engl. 1994, 33, 458-460.
26. [6c] S. Laschat, M. Grehl, Angew. Chem. 1994, 106, 475-478; Angew. Chem. Int. Ed. Engl. 1994, 33, 458-460.
27. [6d] S. Laschat, M. Grehl, Chem. Ber. 1994, 127, 2023-2034.
28. [6e] The fact that the corresponding aldehydes with a terminal alkene do not undergo Lewis-acid-catalyzed cyclization may be taken as evidence against a concerted mechanism. Thus, the intermediate carbenium ion must be stabilized by at least two alkyl substituents.
29. A. Monsees, S. Laschat, S. Kotila, T Fox, E.-U Würthwein, Liebigs Ann./Recueil 1997, 533-540.
30. A. Monsees, S. Laschat, I. Dix, J. Org. Chem. 1998, 63, 10018-10021.
31. [9a] B. J. Kim, Y. S. Park, P. Beak, J. Org. Chem. 1999, 64, 1705-1708.
32. [9b] Y. S. Park, P. Beak, J. Org. Chem. 1997, 62, 1574-1575.
33. [9c] D. J. Gallagher, P. Beak, J. Org. Chem. 1995, 60, 7092-7093.
34. [10a] L. A. Castonguay, J. W. Guiles, A. K. Rappé, A. I. Meyers, J. Org. Chem. 1992, 57, 3819-3821.
35. [10b] A. I. Meyers, D. A. Dickman, M. Boes, Tetrahedron 1987, 43, 5095-5108.
36. [10c] A. I. Meyers, T. M. Sielecki, J. Am. Chem. Soc. 1991, 113, 2789-2790.
37. [11a] R. E. Gawley, Curr. Org. Chem. 1997, 1, 71-94.
38. [11b] R. E. Gawley, K. Rein, S. Chemburkar, J. Org. Chem. 1989, 54, 3002-3004.
39. [11c] K. Rein, M. Goicoechea-Pappas, T. V. Anklebar, G. C. Hart, G. A. Smith, R. E. Gawley, J. Am. Chem. Soc. 1989, 111, 2211-2217.
40. W. J. Close, J. Am. Chem. Soc. 1951, 73, 95-98.
41. [13a] P. Beak, S. T. Kerrick, D. J. Gallagher, J. Am. Chem. Soc. 1993, 115, 10628-10636.
42. [13b] P. Beak, W. J. Zajdel, J. Am. Chem. Soc. 1984, 106, 1010-1018.
43. [I4] A. R. Katritzky, J. Cobo-Domingo, B. Yang, P. J. Steel, Tetrahedron: Asymmetry 1999, 10, 255-263.
44. K. Soai, A. Ookawa, J. Org. Chem. 1986, 51, 4000-4005.
45. A. V. Rama Rao, T. G. Murali Dhar, T. K. Chakraborty, M. K. Gurjar, Tetrahedron Lett. 1988, 29, 2069-2072, and references cited therein.
46. Programs used: InsightII, version 2000; Discover, version 98.0; Force Field CVFF, version 2.3, Molecular Simulations Inc., 2000.
47. A. de Camp Schuda, P. H. Mazzocchi, G. Fritz, T. Morgan, Synthesis 1986, 309-312.
48. [19a] K. Omura, D. Swern, Tetrahedron 1978, 34, 1651-1660.
49. [19b] A. J. Mancuso, S.-L. Huang, D. Swern, J. Org. Chem. 1978, 43, 2480-2482.
50. [19c] A. J. Mancuso, D. Swern, Synthesis 1981, 165-185.
51. [19d] The aldehydes 27 and 33 (optical purity > 95%) were used immediately for cyclization. Purification by flash chromatography or Kugelrohr distillation resulted in complete racemization, as shown by GC on a chiral cyclodextrin-β stationary phase. After storage for 12 h at +4 °C under argon, racemization was also observed.
52. L. E. Overman, L. A. Flippin, Tetrahedron Lett. 1981, 22, 195-198.
53. For cell materials, and sensitivity tests see: [21a] A. Monsees, S. Laschat, M. Hotfilder, J. Wolff, K. Bergander, L. Terfloth, R. Fröhlich, Bioorg. Med. Chem. Lett. 1997, 7, 2945-2950.
54. [21b] M. B. Hansen, S. E. Nielsen, K. Berg, J. Immunol. Methods 1989, 119, 203-210.
55. -1]for RD-ES: 244 (34a), 592 (34b), 164 (35b); and for CAD-ES1: 310 (34a), 307 (34b), 159 (35b).
56. A. Monsees, Dissertation, Technische Universität Braunschweig, 1998.