Synthesis of four atropdiastereoisomers of C-O-D-O-E ring of vancomycin by sequential cycloetherifications

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1403-1406

  Vergne, Caroline ^a   Bois Choussy, Michèle ^a   Beugelmans, René ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

VANCOMYCIN;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584934     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00036-1     Document Type: Article

References (36)

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13. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
14. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
15. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
16. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
17. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
18. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
19. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
20. 7) For selected examples, see: (a) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. J. Chem. Soc., Chem. Commun. 1994, 439-440; (b) Beugelmans, R.; Singh, G. P.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. J. Org. Chem. 1994, 59, 5535-5542; (c) Beugelmans, R.; Bigot, A.; Zhu, J. Tetrahedron Lett. 1994, 35, 7391-7394; (d) Beugelmans, R.; Bourdet, S.; Zhu, J. Tetrahedron Lett. 1995, 36, 1279-1282; (e) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389-6396; f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; (g) Zhu, J.; Bouillon, J. P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7391-7394; (h) Beugelmans, R.; Bigot, R.; Zhu, J. J. Org. Chem. 1996, 61, 771-774;
21. 8) See also: (a) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1995, 5, 3091-3096; (b) Boger, D. L. Zhou, J. J. Org. Chem. 1996, 61, 3938-3939; (c) Rama Rao, A. V.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S. K.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023-26; (d) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254.
22. 8) See also: (a) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1995, 5, 3091-3096; (b) Boger, D. L. Zhou, J. J. Org. Chem. 1996, 61, 3938-3939; (c) Rama Rao, A. V.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S. K.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023-26; (d) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254.
23. 8) See also: (a) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1995, 5, 3091-3096; (b) Boger, D. L. Zhou, J. J. Org. Chem. 1996, 61, 3938-3939; (c) Rama Rao, A. V.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S. K.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023-26; (d) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254.
24. 8) See also: (a) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Biorg. Med. Chem. Lett. 1995, 5, 3091-3096; (b) Boger, D. L. Zhou, J. J. Org. Chem. 1996, 61, 3938-3939; (c) Rama Rao, A. V.; Reddy, K. L.; Rao, A. S.; Vittal, T. V. S. K.; Reddy, M. M.; Pathi, P. L. Tetrahedron Lett. 1996, 37, 3023-26; (d) Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254.
25. 9) Burgess, K.; Lim, D.; Martinez, C. I. Angew. Chem. Int. Ed. Engl. 1996, 35, 1077-1078.
26. 10) Beugelmans, R.; Bois-Choussy, M.; Vergne, C.; Bouillon, J. P.; Zhu, J. J. Chem. Soc., Chem. Commun. 1996, 1029-1030.
27. 11) Sala, T.; Sargent, M. V. J. Chem. Soc. PT I 1979, 2593-2598.
28. 12) (a) Frazer, M. J.; Gerrard, W.; J. Chem. Soc. 1955, 2959-60; (b) Gerrard, W.; Whelans, M. A. J. Chem. Soc. 1956, 4296-4300; (c) Manchard, P. S. J. Chem. Soc., Chem. Commun. 1971, 667.
29. 12) (a) Frazer, M. J.; Gerrard, W.; J. Chem. Soc. 1955, 2959-60; (b) Gerrard, W.; Whelans, M. A. J. Chem. Soc. 1956, 4296-4300; (c) Manchard, P. S. J. Chem. Soc., Chem. Commun. 1971, 667.
30. 12) (a) Frazer, M. J.; Gerrard, W.; J. Chem. Soc. 1955, 2959-60; (b) Gerrard, W.; Whelans, M. A. J. Chem. Soc. 1956, 4296-4300; (c) Manchard, P. S. J. Chem. Soc., Chem. Commun. 1971, 667.
31. 13) (a) Yazawa, H.; Tanaka, K.; Kariyone, K. Tetrahedron Lett. 1974, 3995-3996; (b) Gerrard, W.; Lappert, M. F. Chem. Rev. 1958, 58, 1081-1111.
32. 13) (a) Yazawa, H.; Tanaka, K.; Kariyone, K. Tetrahedron Lett. 1974, 3995-3996; (b) Gerrard, W.; Lappert, M. F. Chem. Rev. 1958, 58, 1081-1111.
33. 3 followed by addition of MeOH gave methyl 3,5-dihydroxy-4-methoxyphenyl acetate quantitatively.
34. 15) The configuration (P or M) of the atropisomer was determined by viewing the atropisomer as helix. "For this designation, only the ligands of highest priority in front and in the back of the framework are considered. If the turn from the priority front ligand to the priority rear ligand is clockwise, the configuration is P, if counterclockwise it is M". See: Eliel, E. L.; Willen, S. H. "Stereochemistry of Organic Compounds" John Wiley & Sons Inc., 1994, Chapter 14.
35. 16) Bois-Choussy, M.; Neuville, L.; Beugelmans, R. Zhu, J. J. Org. Chem. in press.
36. 17) All new compounds gave spectra data consistent with the assigned structures.