Synthesis of a model bicyclic CDE ring system of ristocetin A and observation of a facile inversion of configuration in a 16-membered DE ring model

Journal of Organic Chemistry

Volumn 63, Issue 9, 1998, Pages 3087-3098

  Pearson, Anthony J ^a   Chelliah, Mariappan V ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FENCLONINE; GLYCINE; RISTOCETIN A; TEICOPLANIN;

ARTICLE; CARBOXY TERMINAL SEQUENCE; COMPLEX FORMATION; CROSS LINKING; DRUG CONFORMATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS;

EID: 0032080621     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980060b     Document Type: Article

References (51)

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2. (a) Isolation: McCormick, M. H.; Stark, W. M.; Pittenger, G. E.; Pittenger, R. C.; McGuire, G. M. Antibiot. Annu. 1955-1956, 606. (b) Structure elucidation: Williams, D. H.; Kalman, J. R. J. Am. Chem. Soc. 1977, 99, 2768. Williamson, M. P.; Williams, D. H. J. Am. Chem. Soc. 1981, 103, 6580. Harris, C. M.; Kopecka, H.; Harris, T. M. J. Am. Chem. Soc. 1983, 105, 6915.
3. (a) Isolation: McCormick, M. H.; Stark, W. M.; Pittenger, G. E.; Pittenger, R. C.; McGuire, G. M. Antibiot. Annu. 1955-1956, 606. (b) Structure elucidation: Williams, D. H.; Kalman, J. R. J. Am. Chem. Soc. 1977, 99, 2768. Williamson, M. P.; Williams, D. H. J. Am. Chem. Soc. 1981, 103, 6580. Harris, C. M.; Kopecka, H.; Harris, T. M. J. Am. Chem. Soc. 1983, 105, 6915.
4. (a) Isolation: McCormick, M. H.; Stark, W. M.; Pittenger, G. E.; Pittenger, R. C.; McGuire, G. M. Antibiot. Annu. 1955-1956, 606. (b) Structure elucidation: Williams, D. H.; Kalman, J. R. J. Am. Chem. Soc. 1977, 99, 2768. Williamson, M. P.; Williams, D. H. J. Am. Chem. Soc. 1981, 103, 6580. Harris, C. M.; Kopecka, H.; Harris, T. M. J. Am. Chem. Soc. 1983, 105, 6915.
5. (a) For reviews on the biological activity of vancomycin and related compounds, see: Barna, J. C. J.: Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339. Williams, D. H. Acc. Chem. Res. 1984, 17, 364. (b) For recent articles on mechanism of action, see: Waltho, J. P.: Williams, D. H. J. Am. Chem. Soc. 1989, 111, 2475. Fesik, S. W.; O'Donnell, T. J.; Gampe, R. T., Jr.; Olejniczak, E. T. J. Am. Chem. Soc. 1986, 108, 3165. Mueller, L.; Heald, S. L.; Hempel, J. C.; Jeffs, P. W. J. Am. Chem. Soc. 1989, 111, 496. Prowse, W. G.; Kline, A. D.; Skelton, M. A.; Loncharich, R. J. Biochem. 1995, 34, 9632.
6. (a) For reviews on the biological activity of vancomycin and related compounds, see: Barna, J. C. J.: Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339. Williams, D. H. Acc. Chem. Res. 1984, 17, 364. (b) For recent articles on mechanism of action, see: Waltho, J. P.: Williams, D. H. J. Am. Chem. Soc. 1989, 111, 2475. Fesik, S. W.; O'Donnell, T. J.; Gampe, R. T., Jr.; Olejniczak, E. T. J. Am. Chem. Soc. 1986, 108, 3165. Mueller, L.; Heald, S. L.; Hempel, J. C.; Jeffs, P. W. J. Am. Chem. Soc. 1989, 111, 496. Prowse, W. G.; Kline, A. D.; Skelton, M. A.; Loncharich, R. J. Biochem. 1995, 34, 9632.
7. (a) For reviews on the biological activity of vancomycin and related compounds, see: Barna, J. C. J.: Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339. Williams, D. H. Acc. Chem. Res. 1984, 17, 364. (b) For recent articles on mechanism of action, see: Waltho, J. P.: Williams, D. H. J. Am. Chem. Soc. 1989, 111, 2475. Fesik, S. W.; O'Donnell, T. J.; Gampe, R. T., Jr.; Olejniczak, E. T. J. Am. Chem. Soc. 1986, 108, 3165. Mueller, L.; Heald, S. L.; Hempel, J. C.; Jeffs, P. W. J. Am. Chem. Soc. 1989, 111, 496. Prowse, W. G.; Kline, A. D.; Skelton, M. A.; Loncharich, R. J. Biochem. 1995, 34, 9632.
8. (a) For reviews on the biological activity of vancomycin and related compounds, see: Barna, J. C. J.: Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339. Williams, D. H. Acc. Chem. Res. 1984, 17, 364. (b) For recent articles on mechanism of action, see: Waltho, J. P.: Williams, D. H. J. Am. Chem. Soc. 1989, 111, 2475. Fesik, S. W.; O'Donnell, T. J.; Gampe, R. T., Jr.; Olejniczak, E. T. J. Am. Chem. Soc. 1986, 108, 3165. Mueller, L.; Heald, S. L.; Hempel, J. C.; Jeffs, P. W. J. Am. Chem. Soc. 1989, 111, 496. Prowse, W. G.; Kline, A. D.; Skelton, M. A.; Loncharich, R. J. Biochem. 1995, 34, 9632.
9. (a) For reviews on the biological activity of vancomycin and related compounds, see: Barna, J. C. J.: Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339. Williams, D. H. Acc. Chem. Res. 1984, 17, 364. (b) For recent articles on mechanism of action, see: Waltho, J. P.: Williams, D. H. J. Am. Chem. Soc. 1989, 111, 2475. Fesik, S. W.; O'Donnell, T. J.; Gampe, R. T., Jr.; Olejniczak, E. T. J. Am. Chem. Soc. 1986, 108, 3165. Mueller, L.; Heald, S. L.; Hempel, J. C.; Jeffs, P. W. J. Am. Chem. Soc. 1989, 111, 496. Prowse, W. G.; Kline, A. D.; Skelton, M. A.; Loncharich, R. J. Biochem. 1995, 34, 9632.
10. (a) For reviews on the biological activity of vancomycin and related compounds, see: Barna, J. C. J.: Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339. Williams, D. H. Acc. Chem. Res. 1984, 17, 364. (b) For recent articles on mechanism of action, see: Waltho, J. P.: Williams, D. H. J. Am. Chem. Soc. 1989, 111, 2475. Fesik, S. W.; O'Donnell, T. J.; Gampe, R. T., Jr.; Olejniczak, E. T. J. Am. Chem. Soc. 1986, 108, 3165. Mueller, L.; Heald, S. L.; Hempel, J. C.; Jeffs, P. W. J. Am. Chem. Soc. 1989, 111, 496. Prowse, W. G.; Kline, A. D.; Skelton, M. A.; Loncharich, R. J. Biochem. 1995, 34, 9632.
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14. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
15. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
16. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
17. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
18. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
19. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
20. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
21. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
22. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
23. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
24. (b) The urgency of the problem of vancomycin resistance is evidenced by numerous references in medical bulletins and the popular press: Rowe, P. M. Lancet 1996, 347, 252. Frieden, T. R.; Musiff, S. S.; Low, D. E.; Willey, B. M.; Williams, G.; Faur, Y.; Eisner, W.; Warren, S.; Kreiswirth, B. Lancet 1993, 342, 76. Lewis, R. FDA Consumer 1995, Sep 11. Williams, D. H.; Westwell, M. S. Chemtech 1996, Mar 17. Begley, S.; Brant, M. The End of Antibiotics? Science: A Medical Disaster in the Making. Newsweek 1994 Mar. Roan, S. Bacterium's Immunity to Powerful Drug Bodes Ill. Los Angeles Times 1996, Feb 20. Boodman, S. G. Antibiotic-Resistant Illnesses on the Rise. The Washington Post; Health News Section 1996, Jan 23. Altman, L. K After Causing Worry in the East, A Germ Has Surfaced in the West. The New York Times 1995, Sep 19; Dec 26. Bishop J. E. Bacteria Causing Ear Infection Grow Resistant to Drugs. Wall St. J. 1994, Jun 15. Day, K. The Germ of a Biotech Boom? Firms Seek Products to Fight Antibiotic-Resistant Bacteria. Washington Post 1995, Aug 19. Stinson, S. C. Chem. Eng. News 1996, 74(39), 75-94, 98-100.
25. For recent reports, see: (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791 (b) Rao, A. V. R.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023. Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795. Zhu, J. Synlett 1997, 133. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721, (e) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Braes, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. (f) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419.
26. For recent reports, see: (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791 (b) Rao, A. V. R.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023. Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795. Zhu, J. Synlett 1997, 133. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721, (e) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Braes, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. (f) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419.
27. For recent reports, see: (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791 (b) Rao, A. V. R.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023. Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795. Zhu, J. Synlett 1997, 133. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721, (e) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Braes, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. (f) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419.
28. For recent reports, see: (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791 (b) Rao, A. V. R.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023. Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795. Zhu, J. Synlett 1997, 133. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721, (e) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Braes, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. (f) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419.
29. For recent reports, see: (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791 (b) Rao, A. V. R.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023. Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795. Zhu, J. Synlett 1997, 133. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721, (e) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Braes, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. (f) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419.
30. For recent reports, see: (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791 (b) Rao, A. V. R.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023. Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795. Zhu, J. Synlett 1997, 133. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721, (e) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Braes, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. (f) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419.
31. For recent reports, see: (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791 (b) Rao, A. V. R.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023. Bois-Choussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795. Zhu, J. Synlett 1997, 133. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721, (e) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T.-Y.; Li, H.; Braes, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421. (f) Evans, D. A.; Barrow, J. C.; Watson, P. S.; Ratz, A. M.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M.; Ellman, J. A.; Rychnovsky, S. D.; Lacour, J. J. Am. Chem. Soc. 1997, 119, 3419.
32. Smith, G. G.; Sivaka, T. J. Org. Chem. 1983, 48, 627.
33. The standard Ullmann coupling reaction for the preparation of diaryl ethers cannot be applied when both aromatic substrates have protected amino acid or peptide side chains; see: Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Crimmin, M. J.; Brown, A. G. Tetrahedron Lett. 1990, 31, 2017.
34. The standard Ullmann coupling reaction for the preparation of diaryl ethers cannot be applied when both aromatic substrates have protected amino acid or peptide side chains; see: Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Crimmin, M. J.; Brown, A. G. Tetrahedron Lett. 1990, 31, 2017.
35. The standard Ullmann coupling reaction for the preparation of diaryl ethers cannot be applied when both aromatic substrates have protected amino acid or peptide side chains; see: Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063. Boger, D. L.; Yohannes, D. Tetrahedron Lett. 1989, 30, 2053. Crimmin, M. J.; Brown, A. G. Tetrahedron Lett. 1990, 31, 2017.
36. Pearson, A. J.; Park, J. G. J. Org. Chem. 1992, 57, 1744. Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153. Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581.
37. Pearson, A. J.; Park, J. G. J. Org. Chem. 1992, 57, 1744. Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153. Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581.
38. Pearson, A. J.; Park, J. G. J. Org. Chem. 1992, 57, 1744. Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153. Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581.
39. Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3940. Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536. Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1995, 117, 10585.
40. Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3940. Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536. Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1995, 117, 10585.
41. Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3940. Pearson, A. J.; Zhang, P.; Bignan, G. J. Org. Chem. 1997, 62, 4536. Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1995, 117, 10585.
42. (a) Pearson, A. J.; Chelliah, M. V.; Bignan, G. C. Synthesis 1997, 536.
43. (b) See also: Beugelmans, R.; Bois-Choussy, M.; Vergne, C.; Bouillon, J.; Zhu, J. J. Chem Soc., Chem. Commun. 1996, 1029. Boger, D. L.; Borzilleri, R. M.; Nukui, S. J. Org. Chem. 1996, 61, 3561.
44. (b) See also: Beugelmans, R.; Bois-Choussy, M.; Vergne, C.; Bouillon, J.; Zhu, J. J. Chem Soc., Chem. Commun. 1996, 1029. Boger, D. L.; Borzilleri, R. M.; Nukui, S. J. Org. Chem. 1996, 61, 3561.
45. Mann, M. J.; Pant, N.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1986, 158 and references therein.
46. NAr reactions that lead to formation of diaryl ethers of this type require the use of base at elevated temperature (ca. 40°C) for extended periods of time. For examples, see ref 4b-d.
47. Williams, D. H.; Searle, M. S.; Westwell, M. S.; Mackay, J. P.; Groves, P.; Beauregard, D. A. Chemtracts: Org Chem. 1994, 7, 133.
48. Lee, K. Ph.D. Dissertation, Case Western Reserve University, 1995.
49. We used various coupling methods and found less epimerization with those conditions described in this article, as reported by: Carpino, L. A.; Ionesco, D.; El-Faham, A. J. Org. Chem. 1996, 61, 2460. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397. Carpino, L. A.; El-Faham, A. J. Org. Chem. 1994, 59, 695.
50. We used various coupling methods and found less epimerization with those conditions described in this article, as reported by: Carpino, L. A.; Ionesco, D.; El-Faham, A. J. Org. Chem. 1996, 61, 2460. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397. Carpino, L. A.; El-Faham, A. J. Org. Chem. 1994, 59, 695.
51. We used various coupling methods and found less epimerization with those conditions described in this article, as reported by: Carpino, L. A.; Ionesco, D.; El-Faham, A. J. Org. Chem. 1996, 61, 2460. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397. Carpino, L. A.; El-Faham, A. J. Org. Chem. 1994, 59, 695.