TTN oxidation of mixed halogenated phenols: Synthesis of vancomycin model diaryl ether possessing a chlorine atom

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8791-8794

  Konishi, Hironori ^a   Okuno, Toshiaki ^a   Nishiyama, Shigeru ^a   Yamamura, Shosuke ^a   Koyasu, Katsuya ^b   Terada, Yukimasa ^b  

^a KEIO UNIVERSITY   (Japan)

^b MEIJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; VANCOMYCIN;

ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; HALOGENATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030602227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02033-3     Document Type: Article

References (18)

1. 1. a) Williams, R.M. in "Synthesis of Optically Active α-Amino Acids," Pergamon Press, 1989, 304-394.
2. b) Yamamura, S.; Nishiyama, S. in "Studies in Natural Products Chemistry," ed by Atta-ur-Rahman, Elsevier, 1992, 10, 629-669.
3. c) Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135-2167.
4. 2. Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett., 1994, 35, 5047-5050.
5. 3. a) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542.
6. b) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282.
7. c) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784.
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9. e) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787-8790.
10. f) Boger, D. L.; Borzilleri, Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091-3096.
11. g) Beugelmans, R.; Bigot, A.; Bois-Choussy, M.; Zhu, J. J. Org. Chem. 1996, 61, 111-774.
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13. I) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 57, 3251-3254.
14. 3OD) 2.67-2.76 (1H, complex), 2.98-3.05 (1H, complex), 3.68 (3H, s), 3.78 (3H, s), 4.69 (1H, q, J= 5 Hz), 5.09 (1H, s), 5.39 (1H, s), 6.80 (2H, d, J= 9Hz), 6.96 (1H, d, J= 1.98 Hz), 7.11 (2H, d, J= 9 Hz, overlapped with 1H), 7.71 (2H, s).
15. 5. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621-8624.
16. 6) 1.37 (9H, s), 2.99 (1H, dd, J= 13.4, 7.9 Hz), 3.42 (1H, dd, J= dd, J= 13.4, 5.5 Hz), 3.56 (3H, s), 3.71 (3H, s), 4.35 (1H, broad s), 5.24 (1H, broad d, J= 9.2 Hz), 5.34 (1H, m), 5.98 (1H, s), 6.71 (1H, d, J= 8.4 Hz), 6.76 (1H, broad d, J= 8.8 Hz), 6.82 (1H, d, J= 8.4 Hz), 6.84 (2H, d, J= 8.8 Hz), 7.07 (1H, broad d, J= 8.1 Hz), 7.23 (2H, d, J= 8.8 Hz), 7.34 (1H, s), 7.38 (1H, d, J= 8.1 Hz), 8.51 (1H, broad d, J= 5.9 Hz), 8.86 (1H, d, J= 8.8 Hz), 9.40 (1H, s).
17. 6) 2.97 (1H, dd, J= 7.7, 14 Hz), 3.43 (1H, dd, J= 5.9, 14 Hz), 3.56 (3H, s), 3.73 (3H, s), 4.30 (1H, s), 4.35 (1H, dd, J= 6.5, 14 Hz), 5.32 (1H, d, J= 8.8 Hz), 5.93 (1H, d, J= 1.8 Hz), 6.80 (1H, d, J= 8.4 Hz), 6.85 (3H, complex), 7.05 (1H, broad d, J= 9.9 Hz), 7.08 (1H, d, J= 8.1 Hz), 7.22 (1H, d, J= 8.8 Hz), 7.35 (2H, complex), 8.52 (2H, complex), 9.27 (1H, s).
18. 8. a) Insight II User Guide, ver. 95.0, BIOSYM/Molecular Simulations: San Diego, 1995. b) Discover User Guide, ver. 2.9.7, BIOSYM/Molecular Simulations: San Diego, 1995.