Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones

Organic Letters

Volumn 14, Issue 9, 2012, Pages 2338-2341

  Gerbino, Dario C ^a   Augner, Daniel ^a   Slavov, Nikolay ^a   Schmalz, Hans Günther ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; BENZOPHENONE DERIVATIVE; BIOLOGICAL PRODUCT; DIMETHYL SULFOXIDE; KETONE; PESTALONE; PHTHALIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; SYNTHESIS;

BENZOFURANS; BENZOPHENONES; BIOLOGICAL AGENTS; CATALYSIS; DIMETHYL SULFOXIDE; KETONES; LIGHT; MOLECULAR STRUCTURE;

EID: 84860623984     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300757m     Document Type: Article

References (49)

1. Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds; Academic Press: New York, 1975; Vol. 1, pp 249-264.
2. Knepper, K.; Ziegert, R. E.; Bräse, S. T. Tetrahedron 2004, 60, 8591-8603 and references therein
3. Hung, T. V.; Mooney, B. A.; Prager, R. H.; Tippett, J. M. Aust. J. Chem. 1981, 34, 383-395
4. Patil, L.; Borate, H. B.; Ponde, D. E.; Deshpande, V. H. Tetrahedron 2002, 58, 6615-6620
5. Mal, D.; Pahari, P. Chem. Rev. 2007, 107, 1893-1918
6. Brady, S. F.; Wagenaar, M. M.; Singh, M. P.; Janso, J. E.; Clardy, J. Org. Lett. 2000, 2, 4043-4046
7. Yoganathan, K.; Rossant, C.; Ng, S.; Huang, Y.; Butler, M. S.; Buss, A. D. J. Nat. Prod. 2003, 66, 1116-1117
8. Strobel, G.; Ford, E.; Worapong, J.; Harper, J. K.; Arif, A. M.; Grant, D. M.; Fung, P. C. W.; Chau, R. M. W. Phytochemistry 2002, 60, 179-183
9. Arnone, A.; Assante, G.; Nasini, G.; Strada, S.; Vercesi, A. J. Nat. Prod. 2002, 65, 48-50
10. Mangas-Sanchez, J.; Busto, E.; Gotor-Fernandez, V.; Gotor, V. Org. Lett. 2012, 14, 1444-1447
11. Yadav, J. S.; Sreenivas, M.; Reddy, A. S.; Reddy, B. V. S. J. Org. Chem. 2010, 75, 8307-8310
12. Kuriyama, M.; Ishiyama, N.; Shimazawa, R.; Shirai, R.; Onomura, O. J. Org. Chem. 2009, 74, 9210-9213
13. Zhang, B.; Xu, M. H.; Lin, G. Q. Org. Lett. 2009, 11, 4712-4715
14. See, for instance: Singh, M.; Argade, N. P. J. Org. Chem. 2010, 75, 3121-3124
15. Cowell, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4193-4198
16. Larock, R. C.; Fellows, C. J. Am. Chem. Soc. 1982, 104, 1900-1907
17. Paleo, M. R.; Lamas, C.; Castedo, L.; Dominguez, D. J. Org. Chem. 1992, 57, 2029-2033
18. Ye, Z.; Lv, G.; Wang, W.; Zhang, M.; Cheng, J. Angew. Chem., Int. Ed. 2010, 49, 3671-3674
19. Luo, F.; Pan, S.; Pan, C.; Qian, P.; Cheng, J. Adv. Synth. Catal. 2011, 353, 320-32
20. Ackermann, L.; Pospech, J. Org. Lett. 2011, 13, 4153-4155
21. Phan, D.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608-15609
22. Omura, S.; Fukuyama, T.; Murakami, Y.; Okamoto, H.; Ryu, I. Chem. Commun. 2009, 6741-6743
23. Willis, M. C. Angew. Chem., Int. Ed. 2010, 49, 6026-6027
24. Slavov, N.; Cvengros, J.; Neudörfl, J.-M.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2010, 49, 7588-7591
25. Cueto, M.; Jensen, P. R.; Kauffman, C.; Fenical, W.; Lobkovsky, E.; Clardy, J. J. Nat. Prod. 2001, 64, 1444-1446
26. Cvengros, J.; Neufeind, S.; Becker, A.; Schmalz, H. G. Synlett 2008, 1993-1998
27. Augner, D.; Gerbino, D. C.; Neudörfl, J.-M.; Schmalz, H.-G. Org. Lett. 2011, 13, 5374-5377
28. Kotali, A.; Papapetrou, M.; Dimos, V.; Harris, P. Org. Prep. Proc. Int. 1998, 30, 177-181
29. Kotali, A.; Tsoungas, P. G. Tetrahedron Lett. 1987, 28, 4321-4322
30. Jacq, J.; Einhorn, C.; Einhorn, J. Org. Lett. 2008, 10, 3757-3760
31. Cannizzaro, S. Justus Liebigs Ann. Chem. 1853, 88, 129
32. Tishchenko, V. E. J. Russ. Phys. Chem. Soc. 1906, 38, 355-418
33. Törrmäkangas, O. P.; Koskinen, A. M. P. Recent Res. Dev. Org. Chem. 2001, 225-255
34. Cronin, L.; Manoni, F.; Connor, C. J. O.; Connon, S. J. Angew. Chem., Int. Ed. 2010, 49, 3045-3048
35. Seki, T.; Tachikawa, H.; Yamada, T.; Hattori, H. J. Catal. 2003, 217, 117-126
36. Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4558-4559
37. Sato, T.; Tamura, K.; Maruyama, K.; Ogawa, O.; Imamura, T. J. Chem. Soc., Perkin Trans. 1 1976, 779-783
38. Netto-Ferreira, J. C.; Scaiano, J. C. Can. J. Chem. 1993, 71, 1209-1215
39. Plistil, L.; Solomek, T.; Wirz, J.; Heger, D.; Klan, P. J. Org. Chem. 2006, 71, 8050-8058
40. Kralj, A.; Kehraus, S.; Krick, A.; Eguereva, E.; Kelter, G.; Maurer, M.; Wortmann, A.; Fiebig, H.-H.; König, G. M. J. Nat. Prod. 2006, 69, 955-1000 (Arugosin H)
41. Hashimoto, T.; Tahara, S.; Takaoka, S.; Tori, M.; Asakawa, Y. Chem. Pharm. Bull. 1994, 42, 1528-1530 (Daldinals A-C)
42. Zhang, C.; Ondeyka, J. G.; Herath, K. B.; Guan, G.; Collado, J.; Platas, G.; Pelaez, F.; Leavitt, P. S.; Gurnett, A.; Nare, B.; Liberator, P.; Singh, S. B. J. Nat. Prod. 2005, 68, 611-613 (Tenellones A+B)
43. Hida, T.; Ishii, T.; Kanamaru, T.; Muroi, M. J. Antibiot. 1991, 44, 600-612 (TAN-931)
44. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719-3726
45. Quinkert, G.; Stark, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 637-655
46. Nicolaou, K. C.; Gray, D.; Tae, J. S. Angew. Chem., Int. Ed. 2001, 40, 3675-3678
47. Jurberg, I. D.; Peng, B.; Wöstefeld, E.; Wasserloos, M.; Maulide, N. Angew. Chem., Int. Ed. 2012, 51, 1950-1953
48. Mori, K.; Ehara, K.; Kurihara, K.; Akiyama, T. J. Am. Chem. Soc. 2011, 133, 6166-6169
49. Haibach, M. C.; Deb, I.; De, C. K.; Seidel, D. J. Am. Chem. Soc. 2011, 133, 2100-2103