Tungsten-catalyzed heterocycloisomerization approach to 4,5-dihydro-benzo[b]furans and -indoles

Journal of the American Chemical Society

Volumn 134, Issue 24, 2012, Pages 9946-9949

  Fisher, Ethan L ^a   Wilkerson Hill, Sidney M ^a   Sarpong, Richmond ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURANS; CYCLOISOMERIZATIONS; FUNCTIONALIZATIONS; NATURAL PRODUCTS; TITLE COMPOUNDS;

AROMATIC COMPOUNDS; CATALYSIS; LEAD COMPOUNDS; TUNGSTEN;

ORGANIC POLLUTANTS;

BENZOFURAN DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; NATURAL PRODUCT; PYRROLE DERIVATIVE; TUNGSTEN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HETEROCYCLOISOMERIZATION; ISOMERIZATION; ONE POT SYNTHESIS; REACTION ANALYSIS;

BENZOFURANS; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; CYCLIZATION; INDOLES; ISOMERISM; TUNGSTEN;

EID: 84862571800     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3045647     Document Type: Article

References (40)

1. For isolation of 1 and 2, see: Zidorn, C.; Ellmerer-Müller, E.-P.; Stuppner, H. Helv. Chim. Acta 2000, 83, 2920-2925
2. For biological activity studies of tyrolobibenzyls, see: Zidorn, C.; Spitaler, R.; Ellmerer-Müller, E.-P.; Perry, N. B.; Gerhäuser, C.; Stuppner, H. Z. Naturforsch. 2002, 57c, 614-619
3. In addition to the hibiscones, the furanoterpenoid/furanosteroid family includes viridin, wortmanin, and halenaquinone. For a review, see: Hanson, J. R. Nat. Prod. Rep. 1995, 12, 381-384
4. Koft, E. R.; Smith, A. B. J. Am. Chem. Soc. 1984, 106, 2115-2121
5. Kraus, G. A.; Wan, Z. W. Synlett 2000, 363-364
6. Ungureanu, S.; Meadows, M.; Smith, J.; Duff, D. B.; Burgess, J. M.; Goess, B. C. Tetrahedron Lett. 2011, 52, 1509-1511
7. For isolation of verticillatine A (4), see: Moreira, V. F.; Oliveira, R. R.; Mathias, L.; Braz-Filho, R.; Vieira, I. J. C. Helv. Chim. Acta 2010, 93, 1751-1757
8. For isolation of 5, see: Makarieva, T. N.; Dmitrenok, A. S.; Dmitrenok, P. S.; Grebnev, B. B.; Stonik, V. A. J. Nat. Prod. 2001, 64, 1559-1561
9. For a recent review of the hapalindole family, see: Gademann, K.; Portmann, C. Curr. Org. Chem. 2008, 12, 326-341
10. 4-Bromoindole, which is used for the preparation of C4-substituted prenyl and reverse prenyl indoles, is widely prepared by the method of Hegedus: Harrington, P. J.; Hegedus, L. S. J. Org. Chem. 1984, 49, 2657-2662
11. Mei, T.-S.; Wang, X.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 10806-10807
12. Lindel, T.; Marsch, N.; Adla, S. K. Top. Curr. Chem. 2012, 309, 67-129
13. The C4-substituted 4,5-dihydroindoles were oxidized without isolation, see: Semmelhack, M. F.; Wulff, W.; Garcia, J. L. J. Organomet. Chem. 1982, 240, C5-C10
14. For a recent example, see: Kamikawa, K.; Kinoshita, S.; Furusyo, M.; Takemoto, S.; Matsuzaka, H.; Uemura, M. J. Org. Chem. 2007, 72, 3394-3402
15. For a vacuum pyrolysis synthesis of 4,5-dihydrobenzo[ b ]furans, 4,5-dihydrobenzo[ b ]thiophenes, and 4,5-dihydroindoles, see: Rosen, B. I.; Weber, W. P. Tetrahedron Lett. 1977, 18, 151-154
16. For a recent treatise on metal vinylidenes of Cr, Mo, and W, see: Iwasawa, N. In Metal Vinylidenes and Allenylidenes in Catalysis; Bruneau, C.; Dixneuf, P. H., Eds; Wiley-VCH: Weinheim, 2008; pp 159-191.
17. For a review, see: McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103-3106
18. For a discussion of metallocarbenoid-mediated vinyl-cyclopropane rearrangements, see: Herndon, J. W. Tetrahedron 2000, 56, 1257-1280
19. For a review on divinylcyclopropane rearrangements, see: Hudlicky, T.; Fan, R. L.; Beckers, D. A.; Kozhuskov, S. I. In Methods of Organic Chemistry, Houben-Weyl, 4 th ed.; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol E17c, p 2589.
20. Li, G.; Huang, X.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 6944-6945
21. Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814-1815
22. Bai, Y.; Tao, W.; Ren, J.; Wang, Z. Angew. Chem., Int. Ed. 2012, 51, 4112-4116
23. Zhang, Y.; Liu, F.; Zhang, J. Chem.-Eur. J. 2010, 16, 6146-6150
24. Zhang, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2006, 45, 6704-6707
25. Labsch, S.; Ye, S.; Adler, A.; Neudörf, J.-M.; Schmalz, H.-G. Tetrahedron: Asymm. 2010, 21, 1745-1751
26. Zhang, M.; Zhang, J. Chem. Commun. 2012, 48, 6339-6401
27. Stereoelectronic influences of substituents have also been observed in metal-mediated openings of, for example, methylene cyclopropanes, see: Masarwa, A.; Fürstner, A.; Marek, I. Chem. Commun. 2009, 5760-5762
28. For details on the synthesis of 7a, see: Bartoli, B.; Chouraqui, G.; Parrain, J.-L. Org. Lett. 2012, 14, 122-125 and the Supporting Information.
29. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 4967-4972
30. Donovan, P. M.; Scott, L. T. J. Am. Chem. Soc. 2004, 126, 3108-3112
31. See Wiedemann, S. H.; Lee, C. In Metal Vinylidenes and Allenylidenes in Catalysis; Bruneau, C.; Dixneuf, P. H., Eds; Wiley-VCH: Weinheim, 2008; pp 279-312.
32. Ohe, K.; Yokoi, T.; Miki, K.; Nishino, F.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 526-527
33. Compounds related to 21 are the basis for medicinally active pharmaceuticals, see: Tang, P. C.; Xia, Y.; Hawtin, R. Hexahydro-cyclohepta- pyrrole oxindole as potent kinase inhibitors, U.S. Patent 2004/0186160 A1, Sep. 23, 2004.
34. For a review on N -alkoxyindoles, see: Somei, M. Heterocycles 1999, 50, 1157-1211
35. For original report of the Upjohn dihydroxylation, see: VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973-1976
36. The methylation was conducted using conditions adapted from an earlier report by Noyori and co-workers, see: Morita, Y.; Suzuki, M.; Noyori, R. J. Org. Chem. 1989, 54, 1785-1787
37. Ilardi, E. A.; Isaacman, M. J.; Qin, Y.-C.; Shelly, S. A.; Zakarian, A. Tetrahedron 2009, 65, 3261-3269
38. Gu, Z.; Zakarian, A. Org. Lett. 2011, 13, 1080-1082
39. N -alkoxy indoles are well known to undergo preferential C3 functionalization, see: Somei, M.; Nakajou, M.; Teramoto, T.; Tanimoto, A.; Yamada, F. Heterocycles 1999, 51, 1949-1956
40. For a synthesis of 30 see: Adams, R.; Way, J. W. J. Am. Chem. Soc. 1954, 76, 2763-2769