Synthesis of a tricyclic lactone embodying the ABC-ring system ofstephaoxocanidine, by tin(IV) chloride-assisted sulfonamidoacetal cyclizationand an aromatization promoted by triethylamine

Arkivoc

Volumn 2003, Issue 10, 2003, Pages 178-188

  Bianchi, Darío A ^a   Kaufman, Teodoro S ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

Cyclization; Isoquinolines; Natural products; Stephaoxocanidine; Synthesis

Indexed keywords

5,6 DIMETHOXY 7H,9H PYRANO[3,4,5 IJ]ISOQUINOLIN 9 ONE; 7 BROMO 5,6 DIMETHOXY 7H,9H PYRANO[3,4,5 IJ]ISOQUINOLIN 9 ONE; ACETIC ACID DERIVATIVE; CAMPHORSULFONIC ACID; ETHYL [2 (ACETYLOXYMETHYL 3,4 DIMETHOXYPHENYL) N (2,2 DIMETHOXYETHYL) N (4 METHYLPHENYL)SULFONYL]AMINOACETATE; ISOQUINOLINE DERIVATIVE; LACTONE DERIVATIVE; STEPHAOXOCANIDINE; SULFONIC ACID DERIVATIVE; TIN CHLORIDE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BROMINATION; CYCLIZATION; LACTONIZATION; STEPHANIA;

EID: 0346432497     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (51)

1. (a) Kashiwaba, N.; Morooka, S.; Kimura, M.; Ono, M. J. Nat. Prod. 1996, 59, 803.
2. (b) Kashiwaba, N.; Morooka, S.; Kimura, M.; Ono, M.; Toda, J.; Suzuki, H.; Sano, T. Nat. Prod. Lett. 1997, 9, 177.
3. (a) Deng, J.-Z.; Zhao, S.-X.; Miao, Z.-Ch. Nat. Prod. Lett. 1993, 2, 283.
4. (b) Deng, J.-Z.; Zhao, S.-X. J. Nat. Prod. 1997, 60, 294.
5. da-Cunha, E. V. L.; Cornélio, M. L.; Barbosa-Filho, J. M.; Braz-Filho, R.; Gray, A. I. J. Nat. Prod. 1998, 61, 1140.
6. (a) Pío-Corrêa, M. In Dicionário das Plantas Úteis do Brasil e das Exóticas Cultivadas; Ministério da Agricultura, Rio de Janeiro, Brazil, Ed., 1984, vol. 2, p. 282.
7. (b) Nawawi, A.; Ma, C.; Nakamura, N.; Hattori, M.; Kurokawa, M.; Shiraki, K.; Kashiwaba, N.; Ono, M. Biol. Pharm. Bull. 1999, 22, 268.
8. (c) Zhong-yao-dai-ci-dian (Dictionary of Chinese Crude Drugs). Chiang Su New Medicine College, Ed., Shanghai Scientific Technologic Publisher, Shanghai, China, 1978, p. 2141.
9. (d) Makidono, R.; Makidono, A.; Matsuura, K. Nippon Acta Radiologica 1977, 37, 1153.
10. (a) Buck, K. T. Azafluoranthene and Tropoloisoquinoline Alkaloids. In The Alkaloids, Brossi, A. Ed.; Academic Press, Inc., New York, 1984; vol. 23, pp. 303-325.
11. (b) Paris, R. R.; Moyse, H. In Matiere Medicale; Masson, Paris, 1967, vol. 2, p. 178.
12. (c) Lewis, W. H.; Stonard, R. J.; Porras-Reyes, B.; Mustoe, T. A. U. S. Patent Appl. 5,156,847, 1992; Chem. Abstr. 1992, 117, 245630t.
13. (d) For a proposal on the formation of azafluoranthene alkaloids from tropoloisoquinolines, see: Silverton, J. V.; Kabuto, C.; Buck, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708.
14. (a) Jackson, A. H.; Stewart, G. W. J. Chem. Soc., Chem. Commun. 1971, 149.
15. (b) Charnock, S. A.; Jackson, A. H.; Martin, J. A.; Stewart, G. W. J. Chem. Soc., Perkin Trans. 1 1974, 1911.
16. (c) Birch, A. J.; Jackson, A. H.; Shannon, P. V. R. J. Chem. Soc., Perkin Trans. 1 1974, 2185.
17. (a) Bianchi, D. A.; Kaufman, T. S. Can. J. Chem. 2000, 78, 1165.
18. (b) Kaufman, T. S. Molecules 2000, 5, 491.
19. (c) Larghi, E. L.; Kaufman, T. S. Tetrahedron Lett. 1997, 38, 3159.
20. (d) Ponzo, V. L.; Kaufman, T. S. J. Chem. Soc., Perkin Trans. 1 1997, 3131.
21. (e) Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105.
22. Kaufman, T. S. Heterocycles 2001, 55, 323.
23. (a) Collington, E. W.; Meyers, A. I. J. Org. Chem. 1971, 36, 3044.
24. (b) Hwang, C. K.; Li, W. S.; Nicolau, K. C. Tetrahedron Lett. 1984, 2295.
25. (a) Snyder, D. C. J. Org. Chem. 1995, 60, 2638.
26. (b) Munyemana, F.; Frisque-Hesbain, A.-M.; Devos, A.; Ghosez, L. Tetrahedron Lett. 1989, 30, 3077.
27. (c) De Luca, L.; Giacomelli, G.; Porcheddu, A. Org. Lett. 2002, 4, 553.
28. (d) Yoshida, Y.; Sakakura, Y.; Aso, N.; Okada, S.; Tanabe, Y. Tetrahedron 1999, 55, 2183.
29. Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195.
30. (a) Uenishi, J.; Tomoko, T.; Ueno, T.; Hiraoka, T.; Yonemitsu, O.; Tsukube, H. Synlett 1999, 41.
31. (b) Hrubiec, R. T.; Smith, M. B. Tetrahedron Lett. 1983, 24, 5031.
32. (c) Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Turner-Jones, R. T.; Reamer, R. A.; Roberts, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763.
33. (d) Du Priest, M. T.; Zinke, P. W.; Conrow, R. E.; Kuzmich, D.; Dantanarayana, A. P.; Sproull, S. J. J. Org. Chem. 1997, 62, 9372.
34. (a) Silveira, C. C.; Bernardi, C. R.; Braga, A. L.; Kaufman, T. S. Synlett 2002, 906.
35. (b) Silveira, C. C.; Bernardi, C. R.; Braga, A. L.; Kaufman, T. S. Tetrahedron Lett. 2001, 42, 8947.
36. (a) MacLean, D. B.; Cundasawmy, N. E. Can. J. Chem. 1972, 50, 3028.
37. (b) Nagata, H.; Miyazawa, N.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 2001, 1094.
38. (a) Hori, K.; Hikage, N.; Inagaki, A.; Mori, S.; Nomura, K.; Yoshii, E. J. Org. Chem. 1992, 57, 2888.
39. (b) Castagnani, R.; De Angelis, R.; De Fusco, E.; Gianessi, F.; Misiti, D.; Meloni, D.; Tinti, M. O. J. Org. Chem. 1995, 60, 8318.
40. Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105.
41. (a) Taylor, S. K.; Fried, J. A.; Grassi, Y. N.; Marolewski, A. E.; Pelton, E. A.; Poel, T.-J.; Rezanka, D. S.; Whittaker, M. R. J. Org. Chem. 1993, 58, 7304.
42. (b) Konoike, T.; Araki, Y. J. Org. Chem. 1994, 59, 7849.
43. 50 = 23 μM.
44. (a) Whaley, W. M.; Govindachari, T. R. Org. React. 1951, 6, 74.
45. (b) Herz, W.; Tsai, L. J. Am. Chem. Soc. 1955, 77, 3529.
46. (c) Biandra, A. A.; Wadia, M. S.; Dutta, N. L. Tetrahedron Lett. 1968, 2677.
47. (a) Dubey, S. K.; Kumar, S. J. Org. Chem. 1986, 51, 3407.
48. (b) Pizey, J. S. In Synthetic Reagents, J. Wiley & Sons, New York, vol. 2, 1974, pp. 15-21.
49. (a) Lovins, R. E.; Andrews, L. J.; Keefer, R. M. J. Org. Chem. 1963, 28, 2847.
50. (b) Lovins, R. E.; Andrews, L. J.; Keefer, R. M. J. Org. Chem. 1965, 30, 1577.
51. Blair, J.; Logan, W. R.; Newbold, G. T. J. Chem. Soc. 1956, 2443.