Copper(I)-mediated and microwave-assisted Caryl-O carboxylic coupling: Synthesis of benzopyranones and isolamellarin alkaloids

Journal of Organic Chemistry

Volumn 72, Issue 24, 2007, Pages 9379-9382

  Thasana, Nopporn ^a,b   Worayuthakarn, Rattana ^a   Kradanrat, Phithakpong ^a   Hohn, Elliot ^a   Young, Lauren ^a   Ruchirawat, Somsak ^a,b,c  

^a Toxicology and Management of Chemicals   (Thailand)

^b Research and Innovation   (Thailand)

^c MAHIDOL UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

ISOLAMELLARIN; PYRROLOISOQUINOLINE ALKALOIDS; PYRUVATES;

CARBOXYLIC ACIDS; CATALYST ACTIVITY; COPPER COMPOUNDS; MICROWAVE IRRADIATION; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

ALKALOID DERIVATIVE; BENZOPYRANONE DERIVATIVE; CARBON; CARBOXYLIC ACID; COPPER; ISOLAMELLARIN; ISOQUINOLINE DERIVATIVE; OXYGEN; PYRAN DERIVATIVE; PYRUVIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYST; LACTONIZATION; MICROWAVE IRRADIATION; REACTION ANALYSIS; SYNTHESIS;

ALKALOIDS; ANTINEOPLASTIC AGENTS; CARBOXYLIC ACIDS; CATALYSIS; COPPER; COUMARINS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, CYCLIC; MICROWAVES; MODELS, CHEMICAL;

EID: 36649015992     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701599g     Document Type: Article

References (57)

1. For the reviews on organocopper, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5499.
2. (b) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428-2439.
3. (c) Sawyer, J. S. Tetrahedron 2000, 56, 5045-5065.
4. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1904, 37, 853-857.
5. (b) Ulimann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2389-2391.
6. For selected publications on Cu(I)-catalyzed C-O bond formations, see: (a) Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973-976.
7. (b) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.
8. see also (c) Lipshutz, B. H.; Unger, J. B. Org. Lett. 2007, 9, 1089-1092.
9. (d) He, H.; Wu, Y.-J. Tetrahedron Lett. 2003, 43, 3445-3446.
10. For selected publications on CuTC, see: (a) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979-981.
11. (b) Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4, 983-985.
12. (c) Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3, 91-93.
13. (d) Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3, 2149-2152.
14. (e) Shen, R.; Porco, J. A. Org. Lett. 2000, 2, 1333-1336.
15. (f) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260-11261.
16. (g) Srogl, J.; Liebeskind, L. S. Org. Lett. 2000, 2, 3229.
17. (h) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312-2313.
18. (i) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
19. (a) d'Augustin, M.; Palais, L.; Alexakis, A. Angew. Chem., Int. Ed. 2005, 44, 1376-1378.
20. (b) Wehlan, H.; Dauber, M.; Femaud, M. T. M.; Schuppan, J.; Mahrwald, R.; Ziemer, B.; Carcia, M. E. J.; Koert, U. Angew. Chem., Int. Ed. 2004, 43, 4597-4601.
21. (c) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem., Int. Ed. 2002, 41, 3701-3704.
22. Andersen, R. J.; Faulkner, D. J.; Cun-Heng, H.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 5492-5495.
23. (a) Pla, D.; Marchal, A.; Olsen, C. A.; Francesch, A.; Alvarez, M. J. Org. Chem. 2005, 70, 8231-8234.
24. (b) Handy, S. T.; Zhang, Y.; Bregman, H. J. Org. Chem. 2004, 69, 2362-2366.
25. (c) Ishibashi, F.; Tanabe, S.; Oda, T.; Iwao, M. J. Nat. Prod. 2002, 65, 500-504.
26. (d) Diaz, B.; Guitian, E.; Castedo, L. Synlett 2001, 1164-1166.
27. (e) Peschko, C.; Winklhofer, C.; Steglich, W. Chem. Eur. J. 2000, 6, 1147-1152.
28. (f) Boger, D. L.; Soenen, D. R.; Boyce, C. W.; Hedrick, M. P.; Jin, Q. J. Org. Chem. 2000, 65, 2479-2483.
29. (g) Banwell, M.; Flynn, B.; Hockless, D.; Longmore, R. W.; Rae, A. D. Aust. J. Chem. 1998, 52, 755-765 and references therein.
30. (a) Ploypradith, P.; Petchmanee, T.; Sahakitpichan, P.; Litvinas, N. D.; Ruchirawat, S. J. Org. Chem. 2006, 71, 9440-9448.
31. (b) Ploypradith, P.; Kagan, R. K.; Ruchirawat, S. J. Org. Chem. 2005, 70, 5119-5125.
32. (c) Ploypradith, P.; Mahidol, C.; Sahakitpichan, P.; Wongbundit, S.; Ruchirawat, S. Angew. Chem., Int. Ed. 2004, 43, 866-868.
33. (d) Ploypradith, P.; Jinaglueng, W.; Pavaro, C.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1363-1366.
34. (e) Ruchirawat, S.; Mutarapat, M. Tetrahedron Lett. 2001, 42, 1205-1208.
35. (a) Kluza, J.; Gallego, M. A.; Loyenz, A.; Beauvillian, J. C.; Sousa-Faro, J. M.; Cuevas, C.; Marchetti, P.; Bailly, C. Cancer Res. 2006, 66, 3177-3187.
36. (b) Bailly, C. Curr. Med. Chem. Anticancer Agents. 2004, 4, 363-378.
37. (c) Ridley, C. P.; Reddy, M. V.; Rocha, G.; Bushman, F. D.; Faulkner, D. J. Bioorg. Med. Chem. 2002, 10, 3285-3290.
38. (d) Reddy, M. V.; Rao, M. R.; Rhodes, D.; Hansen, M. S.; Rubins, K.; Bushman, F. D.; Venkateswarlu, Y.; Faulkner, D. J. J. Med. Chem. 1999, 42, 1901-1907 and references therein.
39. Hosoya, T.; Takashiro, E.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 1994, 116, 1004-1015.
40. Koch, K.; Podlech, J.; Pfeiffer, E.; Metzler, M. J. Org. Chem. 2005, 70, 3275-3276.
41. (a) Yao, T.; Yue, D.; Larock, R. C. J. Org. Chem. 2005, 70, 9985-9989.
42. (b) Kraus, G. A.; Zhang, N. J. Org. Chem. 2000, 65, 5644-5646.
43. (c) Chuder, B. A.; Kalinin, A. V.; Taylor, N. J.; Snieckus, V. Angew. Chem., Int. Ed. 1999, 38, 1435-1438.
44. (a) Palencia, H.; Garcia-Jimenez, F.; Takacs, J. M. Tetrahedron Lett. 2004, 45, 3849-3853.
45. (b) Langer, P.; Saleh, N. N. R.; Freifeld, I. Chem. Commun. 2002, 168-169.
46. (c) Muraki, T.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1999, 1713-1716.
47. For microwave irradiation, see: (a) Kappe, C. O.; Stadler, A. In Microwaves in Organic and Medicinal Chemistry; Mannhold, R., Kubinyi, H., Folkers, G., Eds.; Wiley-VCH: Weinheim, 2005.
48. (b) Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, 2002.
49. (c) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 44, 6250-6284.
50. Sahakitpichan, P.; Thasana, N.; Ruchirawat, S. Synthesis 2005, 2934-2938.
51. Lactone 5e was obtained in only 3% yield from 3-(2-chlorophenyl)- indole-2-carboxylic acid under conventional heating, refluxing DMF overnight,and lactone 5f was obtained in 7% yield from 2-(2-chlorophenyl)-indole-3- carboxylic acid. Reaction with (2-bromophenyl)indole carboxylic acid derivatives showed no lactone formation under the same conditions.
52. Thasana, N.; Prachyawarakorn, V.; Tontoolarag, S.; Ruchirawat, S. Tetrahedron Lett. 2003, 44, 1019-1021.
53. (a) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395.
54. (b) Coutrot, P.; Grison, C.; Tabyaoni, M.; Czernecki, S.; Valery, J.-M. J. Chem. Soc., Chem. Commun. 1988, 1515-1516.
55. (a) Casagrande, C.; Invernizzi, A.; Ferrari, G.; Ferrini, R. J. Med. Chem. 1968, 11, 765-770.
56. (b) Alberola, A.; Ortega, A. G.; Sádaba, M. L.; Sañudo, C. Tetrahedron 1999, 55, 6555-6566.
57. For complete characterization of compound 5, see the Supporting Information.