Nickel-catalyzed synthesis of benzocoumarins: Application to the total synthesis of arnottin I

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8312-8315

  Madan, Sachin ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOCOUMARINS; NICKEL-CATALYZED SYNTHESIS; OXABENZONORBORNADIENES;

ACETONITRILE; CATALYST ACTIVITY; NICKEL; POWDER METALS; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

ARNOTTIN I; BENZOCOUMARIN DERIVATIVE; CATECHOL; COUMARIN DERIVATIVE; NATURAL PRODUCT; NICKEL; UNCLASSIFIED DRUG; ZINC;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH TEMPERATURE; POWDER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STRUCTURE ANALYSIS; TEMPERATURE SENSITIVITY;

CATALYSIS; COUMARINS; CYCLIZATION; IODOBENZOATES; NICKEL; NORBORNANES;

EID: 33750007035     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061477h     Document Type: Article

References (54)

1. For isolation and structure elucidation of gilvocarcin V and M, see: (a) Horii, S.; Fukase, H.; Mizuta, E.; Hatano, K.; Mizuno, K. Chem. Pharm. Bull. 1980, 28, 3601.
2. (b) Nakano, H.; Matsuda, Y.; Ito, K.; Ohkubo, S.; Morimoto, M.; Tomita, F. J. Antibiot. 1981, 34, 266.
3. (c) Takahashi, K.; Yoshida, M.; Tomita, F.; Shirahata, K. J. Antibiot. 1981, 34, 266.
4. (d) Hirayama, N.; Takahashi, K.; Shirahata, K.; Ohashi, Y.; Sasada, Y. Bull. Chem. Soc. Jpn. 1981, 54, 1338.
5. (e) Balitz, D. M.; O'Herron, F. A.; Bush, J.; Vyas, D. M.; Nettleton, D. E.; Grulich, R. E.; Bradner, W. T.; Doyle, T. W.; Arnold, E.; Clardy, J. J. Antibiot. 1981, 34, 1544.
6. (f) Jain, T. C.; Simolike, G. C.; Jackman, L. M. Tetrahedron 1983, 39, 599.
7. For the total synthesis of gilvocarcin V and M, see: (g) Matsumoto, T.; Hosoya, T.; Suzuki, K. J. Am. Chem. Soc. 1992, 114, 3568.
8. (h) Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004.
9. For isolation and structure determination of ravidomycin, see: (a) Findlay, J. A.; Liu, J.-S.; Radics, L.; Rakhit, S. Can. J. Chem. 1981, 59, 3018.
10. (b) Findlay, J. A.; Liu, J.-S.; Radics, L. Can. J. Chem. 1983, 61, 323.
11. (c) Narita, T.; Matsumoto, M.; Mogi, K.; Kukita, K.; Kawahara, R.; Nakashima, T. J. Antibiot. 1989, 42, 347.
12. For the total synthesis of ravidomycin, see: (d) Futagami, S.; Ohashi, Y.; Imura, K.; Ohmori, K.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 2000, 41, 1063.
13. For chrysomycin A and B, see: (a) Strelitz, F.; Flon, H.; Asheshov, I. N. J. Bacteriol. 1955, 69, 280.
14. (b) Weiss, U.; Yoshihira, K.; Highet, R. J.; White, R. J.; Wei, T. T. J. Antibiot. 1982, 35, 1194.
15. For an excellent review on aryl C-glycoside antibiotics, see: Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1-65.
16. For isolation and structure of defucogilvocarcin V, see: (a) Misra, R.; Tritch, H. R., III; Pandey, R. C. J. Antibiot. 1985, 38, 1280.
17. (b) Defucogilvocarcin M: Nakashima, T.; Fujii, T.; Sakai, K.; Sameshima, T.; Kumagai, H.; Yoshioka, T. PCT Patent Appl. W098/22612 A1, 1998; Chem. Abstr. 1998, 129, 49638.
18. For the total synthesis of defucogilvocarcins, see: (c) Macdonald, S. J. F.; McKenzie, T. C.; Hassen, W. D. J. Chem. Soc., Chem. Commun. 1987, 1528.
19. (d) Patten, A. D.; Nguyen, N. H.; Danishefsky, S. J. J. Org. Chem. 1988, 53, 1003.
20. (e) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1988, 29, 2517.
21. (f) McGee, L. R.; Confalone, P. N. J. Org. Chem. 1988, 53, 3695.
22. (g) Hart, D. J.; Merriman, G. H. Tetrahedron Lett. 1989, 30, 5093.
23. (h) Deshpande, P. P.; Martin O. R. Tetrahedron Lett. 1990, 2931, 6313.
24. (i) Parker, K. A.; Coburn, C. A. J. Org. Chem. 1991, 56, 1666.
25. (j) Hua, D. H.; Saha, S.; Roche, D.; Maeng, J. C.; Iguchi, S.; Baldwin, C. J. Org. Chem. 1992, 57, 399.
26. (k) Takemura, I.; Imura, K.; Matsumoto, T.; Suzuki, K. Org. Lett. 2004, 6, 2503.
27. For isolation and structure determination of arnottin I, see: (a) Ishii, H.; Ishikawa, T.; Murota, M.; Aoki, Y.; Harayama, T. J. Chem. Soc., Perkin Trans. 1 1993, 1019.
28. (b) Ishii, H.; Ishikawa, T.; Haginiwa, J. Yakugaku Zasshi 1977, 97, 890.
29. (a) Harayama, T.; Yasuda, H.; Akiyama, T.; Takeuchi, Y.; Abe, H. Chem. Pharm. Bull. 2000, 48, 861.
30. (b) Harayama, T.; Yasuda, H. Heterocycles 1997, 46, 61.
31. (a) Rayabarapu, D. K.; Cheng, C.-H. J. Am. Chem. Soc. 2002, 124, 5630.
32. (b) Huang, Y.-C.; Majumdar, K. K.; Cheng, C.-H. J. Org. Chem. 2002, 67, 1682.
33. (c) Rayabarapu, D. K.; Cheng, C.-H. Chem. Commun. 2002, 942.
34. (d) Shanmugasundaram, M.; Wu, M.-S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233.
35. (e) Hsiao, T.-Y.; Santhosh, K. C.; Liou, K.-F.; Cheng, C-H. J. Am. Chem. Soc. 1998, 120, 12232.
36. (a) Rayabarapu, D. K.; Yang, C.-H.; Cheng, C.-H. J. Org. Chem. 2003, 68, 6726.
37. (b) Rayabarapu, D. K.; Cheng, C.-H. Chem.-Eur. J. 2003, 9, 3164.
38. (c) Rayabarapu, D. K.; Chiou, C.-F.; Cheng, C.-H. Org. Lett. 2002, 4, 1679.
39. (d) Huang, D.-J.; Rayabarapu, D. K.; Li, L.-P.; Sambaiah, T.; Cheng, C.-H. Chem.-Eur. J. 2000, 6, 3706.
40. (e) Sambaiah, T.; Huang, D.-J.; Cheng, C.-H. New J. Chem. 1998, 22, 1147.
41. (f) Shukla, P.; Cheng, C.-H. Org. Lett. 2006, 8, 2867.
42. (a) Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry. Wiley: New York, 1982.
43. (b) Naser-Hijazi, B.; Stolze, B.; Zanker, K. S. Second Proceedings of the International Society of Coumarin Investigators; Springer: Berlin, 1994.
44. (c) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon Press: Oxford, 1984; Vol. 3. Chapter 2.24, pp 799-810.
45. (d) Staunton, J. In Comprehensive Heterocyclic Chemistry; Barton, D. H. R., Ollis, W. D., Sammes, P. G., Eds.: Pergamon Press: Oxford. 1979; Vol. 4, Chapter 18.2, pp 651-653.
46. Dyke, S. F.; Tiley, E. P. Tetrahedron 1975, 31, 561.
47. Rayabarapu, D. K.; Shukla, P.; Cheng, C.-H. Org. Lett. 2003, 5, 4903.
48. Taylor, E. C.; Kienzle, F.; Robey, R.; McKillop, A. J. Am. Chem. Soc. 1970, 92, 2175.
49. Kohn, M. J. Am. Chem. Soc. 1951, 73, 480.
50. (a) Eicher, T.; Ott, M.; Speicher, A. Synthesis 1996, 755.
51. (b) Stoltz, B. M.; Kano, T.; Corey, E. J. J. Am. Chem. Soc. 2000, 122, 9044.
52. Hu, M.; Brasseur, N.; Yildiz, S. z.; van Lier, J. E.; Leznoff, C. C. J. Med. Chem. 1998, 41, 1789.
53. Stringer, M. B.; Wege, D. Tetrahedron Lett. 1980, 21, 3831.
54. Rayabarapu, D. K.; Sambaiah, T.; Cheng, C.-H. Angew. Chem., Int. Ed. 2001, 40, 1286.