Nonconventional stereochemical issues in the design of the synthesis of the vancomycin antibiotics: Challenges imposed by axial and nonplanar chiral elements in the heptapeptide algycons

Angewandte Chemie - International Edition

Volumn 37, Issue 19, 1998, Pages 2704-2708

  Evans, David A ^a   Dinsmore, Christopher J ^a   Watson, Paul S ^a   Wood, Michael R ^a   Richardson, Timothy I ^a   Trotter, B Wesley ^a   Katz, Jeffrey L ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Antibiotics; Atropisomerism; Chirality; Nucleophilic aromatic substitutions; Vancomycin

Indexed keywords

EID: 0032538360     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2704::AID-ANIE2704>3.0.CO;2-1     Document Type: Article

References (30)

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2. D. A. Evans, M. R. Wood, B. W. Trotter, T. I. Richardson, J. C. Barrow, J. L. Katz, Angew. Chem. 1998, 110, 2864-2868; Angew. Chem. Int. Ed. 1998, 37, 2700-2704.
3. For a general discussion of chirality in structures devoid of chiral centers see: E. L. Eliel, S. H. Wilen, Stereochemistry of Carbon Compounds, Wiley, New York, 1994, Chapter 14, pp. 1119-1190. See p 1193 for the definition of atropisomerism.
4. a) Ureido-balhimycin structure: G. M. Sheldrick, E. Paulus, L. Vertesy, F. Hahn, Acta Crystallogr. Sect. B 1995, 51, 89-98; b) Vancomycin structure: M. Schäfer, T. R. Schneider, G. M. Sheldrick, Structure, 1996, 4, 1509-1515.
5. a) Ureido-balhimycin structure: G. M. Sheldrick, E. Paulus, L. Vertesy, F. Hahn, Acta Crystallogr. Sect. B 1995, 51, 89-98; b) Vancomycin structure: M. Schäfer, T. R. Schneider, G. M. Sheldrick, Structure, 1996, 4, 1509-1515.
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9. The seven amino acid residues are numbered consecutively, starting from the amino terminus. The M(X-Y) nomenclature refers to the macrocycle containing an oxidative crosslink between aryl groups of residues X and Y. Bicyclic moieties will be identified as M(X-Y)(Y-Z).
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13. For the synthesis of orienticin C aglycon see: a) D. A. Evans, C. J. Dinsmore, A. M. Ratz, D. A. Evrard, J. C. Barrow, J. Am. Chem. Soc. 1997, 119, 3417-3418; b) D. A. Evans, J. C. Barrow, P. S. Watson, A. M. Ratz, C. J. Dinsmore, D. A. Evrard, K. M. DeVries, J. A. Ellman, S. D. Rychnovsky, J. Lacour, J. Am. Chem. Soc. 1997, 119, 3419-3420.
14. For the synthesis of orienticin C aglycon see: a) D. A. Evans, C. J. Dinsmore, A. M. Ratz, D. A. Evrard, J. C. Barrow, J. Am. Chem. Soc. 1997, 119, 3417-3418; b) D. A. Evans, J. C. Barrow, P. S. Watson, A. M. Ratz, C. J. Dinsmore, D. A. Evrard, K. M. DeVries, J. A. Ellman, S. D. Rychnovsky, J. Lacour, J. Am. Chem. Soc. 1997, 119, 3419-3420.
15. For model studies directed toward the construction of the M(5-7) biaryl linkage see: a) K. C. Nicolaou, X.-J. Chu, J. M. Ramanjulu, S. Natarajan, S. Bräse, F. Rübsam, C. N. C. Boddy, Angew. Chem. 1997, 109, 1551-1552; Angew. Chem. Int. Ed. Engl. 1997, 36, 1539-1540; b) K. C. Nicolaou, J. M. Ramanjulu, S. Natarajan, S. Bràse, H. Li, C. N. C. Boddy, Chem. Commun. 1997, 1899-1900.
16. For model studies directed toward the construction of the M(5-7) biaryl linkage see: a) K. C. Nicolaou, X.-J. Chu, J. M. Ramanjulu, S. Natarajan, S. Bräse, F. Rübsam, C. N. C. Boddy, Angew. Chem. 1997, 109, 1551-1552; Angew. Chem. Int. Ed. Engl. 1997, 36, 1539-1540; b) K. C. Nicolaou, J. M. Ramanjulu, S. Natarajan, S. Bràse, H. Li, C. N. C. Boddy, Chem. Commun. 1997, 1899-1900.
17. For model studies directed toward the construction of the M(5-7) biaryl linkage see: a) K. C. Nicolaou, X.-J. Chu, J. M. Ramanjulu, S. Natarajan, S. Bräse, F. Rübsam, C. N. C. Boddy, Angew. Chem. 1997, 109, 1551-1552; Angew. Chem. Int. Ed. Engl. 1997, 36, 1539-1540; b) K. C. Nicolaou, J. M. Ramanjulu, S. Natarajan, S. Bràse, H. Li, C. N. C. Boddy, Chem. Commun. 1997, 1899-1900.
18. Abbreviations: Tfa: trifluoroacetyl; TFA: trifluoroacetic acid; DMSO: dimethyl sulfoxide; Boc: tert-butoxycarbonyl; NOE: nuclear Overhauser effect; Tf: trifluoromethanesulfonyl; Ms: methanesulfonyl; Ac:acetyl; Ddm: 4,4Õdimethoxydiphenylmethyl; Bn: benzyl; DCB: 3,4-dichlorobenzyl; Piv: pivaloyl.
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25. 1H NOE data for protons on the nitro-containing aromatic ring; their positions may be established relative to the benzylic hydroxyl-bearing stereocenters para to the diaryl ether linkage.
26. D. A. Evans, P. S. Watson, Tetrahedron Lett. 1996, 37, 3251-3254.
27. Similar observations have been made in monocyclic model systems. a) D. L. Boger, R. M. Borzilleri, S. Nukui, Bioorg. Med. Chem. Lett. 1995, 5, 3091-3096; b) D. L. Boger, R. M. Borzilleri, S. Nukui, R. T. Beresis, J. Org. Chem. 1997, 62, 4721-4736.
28. Similar observations have been made in monocyclic model systems. a) D. L. Boger, R. M. Borzilleri, S. Nukui, Bioorg. Med. Chem. Lett. 1995, 5, 3091-3096; b) D. L. Boger, R. M. Borzilleri, S. Nukui, R. T. Beresis, J. Org. Chem. 1997, 62, 4721-4736.
29. 3, DMF, 45°C) proceeding with negligible atropselectivity has recently been reported: D. L. Boger, R. T. Beresis, O. Loiseleur, J. H. Wu, S. L. Castle, Bioorg. Med. Chem. Lett. 1998, 8, 721-724.
30. The option of thermal atropisomer equilibration of the M(2-4) and M(4-6) rings is also possible. Boger et al. have begun to explore these processes: D. L. Boger, O. Loiseleur, S. L. Castle, R. T. Beresis, J. H. Wu, Bioorg. Med. Chem. Lett. 1997, 7, 3199-3202. See also ref. [16b].