Synthesis of azabenzisochromanquinone antibiotics, I: Hetero Diels-Alder reactions of isochromanquinones with 1-aza-1,3-dienes

Liebigs Annales

Volumn , Issue 9, 1996, Pages 1385-1394

  Tödter, Carsten ^a   Lackner, Helmut ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Antibiotics; Azabenzisochromanquinones; Hetero Diels Alder reactions; Structure activity relations

Indexed keywords

EID: 0346453862     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960908     Document Type: Article

References (48)

1. H. Lackner, B. Hoffmann, A. Schönebaum, Liebigs Ann. Chem. 1993, 333;
2. B. Hoffmann, H. Lackner, Liebigs Ann. 1995, 87.
3. S. Takano, K. Hasuda, A. Ito, Y. Koide, F. Ishii, I. Haneda, S. Chihara, Y. Koyama, J. Antibiot. 1976, 29, 765;
4. N. Tanaka, T. Okabe, F. Isono, M. Kashiwagi, K. Nomoto, A. Shimadzu, T. Nishimura, J. Antibiot. ibid. 1985, 38, 1327;
5. J. Krupa, Ph. D. Thesis, University of Göttingen, 1986.
6. S. Omura, Y. Iwai, K. Hinotozawa, H. Tanaka, Y. Takahashi, A. Nakagawa, J. Antibiot. 1982, 35, 1425;
7. M. Murata, T. Miyasaka, H. Tanaka, S. Omura, J. Antibiot. ibid. 1985, 38, 1025.
8. T. Arai, K. Yazawa, Y. Mikami, A. Kubo, K. Takahashi, J. Antibiot. 1976, 29, 398;
9. Y. Mikami, K. Yokoyama, A. Omi, T. Arai, J. Antibiot. ibid. 1976, 29, 408.
10. M. Kono, Y. Saitoh, K. Shirahata, Y. Arai, S. Ishii, J. Am. Chem. Soc. 1987, 109, 7224;
11. K. Shimomura, O. Hirai, T. Mizota, S. Matsumoto, J. Mori, F. Shimbayama, H. Kikuchi, J. Antibiot. 1987, 40, 600.
12. P. Withopf, Ph. D. Thesis, University of Göttingen, 1990.
13. F. Hesse, Diploma Thesis, University of Göttingen, 1993.
14. C. Tödter, Diploma Thesis, University of Göttingen, 1992.
15. T. Kometani, Y. Takeuchi, E. Yoshii, J. Chem. Soc., Perkin Trans. 1, 1981, 1197;
16. G. A. Kraus, M. T. Molina, J. A. Walling, J. Chem. Soc., Chem. Commun. 1986, 1568;
17. C. Saitz B., J. A. Valderrama, R. Tapia, F. Farina, M. C. Paredes, Synth. Commun. 1992, 22, 955.
18. P. Nebois, R. Barret, H. Fillion, Tetrahedron Lett. 1990, 31, 2569;
19. Y. Kitahara, A. Kubo, Heterocycles 1992, 34, 1089;
20. B. Ocana, M. Espada, C. Avendano, Tetrahedron 1995, 51, 1253.
21. L. M. Harwood, J. Chem. Soc., Perkin Trans. 1, 1984, 2577.
22. D. W. Cameron, D. G. I. Kingston, N. Sheppard, A. Todd, J. Chem. Soc. 1964, 98;
23. T. Kometani, E. Yoshii, J. Chem. Soc., Perkin Trans. 1, 1981, 1191.
24. G. A. Kraus, J. Shi, D. Reynolds, J. Org. Chem. 1990, 55, 1105.
25. M. C. Kloetzel, R. P. Dayton, B. Y. Abadir, J. Org. Chem. 1955, 20, 38.
26. R. V. Hoffman, H. O. Kim, J. Org. Chem. 1991, 56, 1014.
27. G. A. Kraus, B. Roth, J. Org. Chem. 1978, 43, 4923.
28. H. Uno, J. Org. Chem. 1986, 51, 350.
29. A. Schönebaum, Ph. D. Thesis, University of Göttingen, 1990.
30. G. A. Kraus, H. Cho, S. Crowley, B. Roth, H. Sugimoto, S. Prugh, J. Org. Chem. 1983, 48, 3439.
31. M. Gude, Ph. D. Thesis, University of Göttingen, 1996.
32. K. Nomura, K. Okazaki, K. Hori, E. Yoshii, Chem. Pharm. Bull. 1986, 34, 3175.
33. E. Gomez-Bengoa, A. M. Echavarren, J. Org. Chem. 1991, 56, 3497;
34. E. J. Corey, D. Enders, Chem. Ber. 1978, 111, 1337;
35. T. Severin, G. Wanninger, H. Lerche, Chem. Ber. ibid. 1984, 117, 2875.
36. H. Lerche, T. Severin, Chem. Ber. 1978, 111, 1195.
37. C. Gesto, E. de la Cuesta, C. Avendano, Tetrahedron 1989, 45, 4477.
38. D. Seebach, M. Pohmakotr, Tetrahedron 1981, 37, 4047.
39. S. Ma, X. Lu, Z. Li, J. Org. Chem. 1992, 57, 709;
40. C. Meyer, I. Marek, J. F. Normant, Synlett 1993, 386.
41. J. A. Valderrama, H. Pessoa-Mahana, R. Tapia, J. Heterocycl. Chem. 1992, 29, 1177.
42. L. Lombardo, Tetrahedron Lett. 1985, 26, 381.
43. a with C-5, C-4a, C-10a, and C-11 or for 33 and 38; 4-H with C-5, C-4a, and C-10a and in both cases: 9-H with C-10.
44. The "Δδ(C-10a/4a) rule" is based on the general finding (compare Table 1) that the differences between the δ values of C-10a and C-4a range from 2.3 to 3.4 for 6-aza regioisomers and from 6.3 to 6.9 for 9-aza compounds (eleutherins and epinanaomycins). The less symmetric 1-methylkalafungins, not causing any regioselectivity problems, show the same tendency: the Δδ values for 6-isomers (33-39) range from 15.1 to 16.8, for the 9-isomer 32 Δδ = 19.5 was found.
45. D. Tadic, B. K. Cassels, M. Leboeuf, A. Cavé, Phytochemistry 1987, 26, 537.
46. C. Tödter, Ph. D. Thesis, University of Göttingen, 1995.
47. The combustion analyses were abandoned in the case of oily or resinous substances or for the precious final products (Scheme 2). Purity and uniformity were controlled very carefully by accurate NMR and mass spectra.
48. 2.