Diaryl ethers using fischer chromium carbene mediated benzannulation

Organic Letters

Volumn 1, Issue 11, 1999, Pages 1721-1723

  Pulley, Shon R ^a   Sen, Subhabrata ^a   Vorogushin, Andrei ^a   Swanson, Erika ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CHROMIUM; DIPHENYL ETHER DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS; ULTRASOUND;

ALKYNES; CHROMIUM; CYCLIZATION; ORGANOMETALLIC COMPOUNDS; PHENYL ETHERS; ULTRASONICS;

EID: 0033518048     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990949u     Document Type: Article

References (36)

1. For general reviews see: (a) Itokawa, H.; Takeya, K. Heterocycles 1993,35, 1467-1501.
2. (b) In Glyopeptide Antibiotics;Nagarajan, R., Ed.; Marcel Decker, Inc.: New York; 1994.
3. Kase, H.; Kaneka, M.; Yamada, K. J. Antibiot. 1987, 40, 450-454.
4. Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. Engl. 1999, 38, 1172-1193.
5. For reviews on the chemistry of ellagitannins, see: (a) Quideau, S.; Feldman, K. S. Chem. Rev. 1996, 96, 475-503.
6. (b) Plant Polyphenols Synthesis, Properties, Signiflcnace; Hemingway, R. W., Lacs, P. E., Eds.; Plenum: New York, 1992.
7. Okuda, T.; Yoshida, T.; Hatano, T. Phytochemistry 1993, 32, 507-521.
8. Miroy, G. J.; Lai, Z.; Lashuel, H. A.; Peterson, S. A.; Strang, C.; Kelly, J. W. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 15051-15056.
9. For reviews, see: (a) Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135-2167.
10. (b) Evans, D. A.; DeVries, K. D. In Glycopeptide Antibiotics; Nagarajan, R., Ed.; Marcel Dekker: New York; 1994; pp 63-103.
11. For recent work with the Ullmann reaction, see: (a) Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986-2987.
12. (b) Jung, M. E.; Lazarova, T. I. J. Org. Chem. 1999, 64, 2976-2977.
13. Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3940-3941.
14. Crimmin, M. J.; Brown, A. G. Tetrahedron Lett. 1990, 31, 2017-2020.
15. For this and related methods, see: Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815-8824.
16. Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421-3422.
17. (a) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378 and references therein.
18. (b) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224-3225 and references therein.
19. Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067.
20. For a Robinson annulation, see: Feng, X.; Edstrom, E. D. Tetrahedron: Asymmetry 1999, 10, 99-105.
21. Olsen, R. K.; Feng, X.; Campbell, M.; Shao, R.-L.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
22. (a) Feldman, K. S.; Sahasrabudhe, K. J. Org. Chem. 1999, 64, 209-216.
23. (b) Feldman, K. S.; Quideau, S.; Appel, J. M. J. Org. Chem. 1996, 61, 6656-6665.
24. (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644-645.
25. (b) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Perganom: Oxford, 1995; Vol. 12, pp 469-547.
26. Pulley, S. R.; Vorogushin, A.; Sen, S. Abstracts of Papers; 215th National Meeting of the American Chemical Society, Dallas, TX; American Chemical Society: Washington, DC, 1998; ORGN 0374.
27. Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D. Organometallics 1998, 17, 4298-4308.
28. See ref 18 and (a) Fischer, E. O.; Kalbfus, W. J. Organomet. Chem. 1972, 46, C15-C18.
29. (b) Connor, J. A.; Jones, E. M. J. Chem. Soc. Part A 1971, 3368-3372.
30. Fischer, E. O.; Maasböl, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 580.
31. Torrent, M.; Duran, M.; Solà M. J. Am. Chem. Soc. 1999. 121, 1309-1316 and references therein.
32. Harrity, J. P. A.; Kerr, W. J.; Middlemiss, D. Tetrahedron 1993, 49, 5565-5576.
33. Leukart, O.; Caviezel, M.; Eberle, A.; Escher, E.; Tun-Kyi, A.; Schwyzer, R. Helv. Chim. Acta. 1976m 6m 2181-2183.
34. (a) Garner, P.; Park, J. M. Org. Synth. 1991, 70, 18-28.
35. (b) Meffre, P.; Gauzy, L.; Peridgues, C.; Desanges-Levecque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877-880.
36. 13C NMR spectra for 5b-d, 6, 7a-e 8a-c, 9-12, 15, 17b, and 18. This material is available free of charge via the Internet at http://pubs.acs.org.