Total synthesis of vancomycin aglycon - Part 2: Synthesis of amino acids 1-3 and construction of the AB-COD-DOE ring skeleton

Angewandte Chemie - International Edition

Volumn 37, Issue 19, 1998, Pages 2714-2716

  Nicolaou, K C ^a,b   Jain, Nareshkumar F ^a,b   Natarajan, Swaminathan ^a,b   Hughes, Robert ^a,b   Solomon, Michael E ^a,b   Li, Hui ^a,b   Ramanjulu, Joshi M ^a,b   Takayanagi, Masaru ^a,b   Koumbis, Alexandros E ^a,b   Bando, Toshikazu ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amino acids; Antibiotics; Natural products; Synthetic methods; Vancomycin

Indexed keywords

EID: 0032538577     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19981016)37:19<2714::aid-anie2714>3.0.co;2-%23     Document Type: Article

References (10)

1. Preceding communication: K. C. Nicolaou, S. Natarajan, H. Li, N. F. Jain, R. Hughes, M. Solomon, J. Ramanjulu, C. N. C. Boddy, M. Takayanagi, Angew. Chem. 1998, 109, 2872-2878; Angew. Chem. Int. Ed. 1998, 37, 2708-2714.
2. Preceding communication: K. C. Nicolaou, S. Natarajan, H. Li, N. F. Jain, R. Hughes, M. Solomon, J. Ramanjulu, C. N. C. Boddy, M. Takayanagi, Angew. Chem. 1998, 109, 2872-2878; Angew. Chem. Int. Ed. 1998, 37, 2708-2714.
3. For a similar procedure, see: A. V. R. Rao, T. K. Chakraborty, K. L. Reddy, A. S. Rao, Tetrahedron Lett. 1994, 35, 5043-5046.
4. K. C. Nicolaou, C. N. C. Boddy, S. Natarajan, T. Y. Yue, H. Li, S. Bräse J. M. Ramanjulu, J. Am. Chem. Soc. 1997, 119, 3421-3422.
5. For a previous synthesis of an AB-COD-DOE ring framework related to vancomycin, see: D. A. Evans, J. C. Barrow, P. S. Watson, A. M. Ratz, C. J. Dinsmore, D. A. Evrard, K. M. D eVries, J. A. Ellman, S. D. Rychnovsky, J. Lacour, J. Am. Chem. Soc. 1997, 119, 3419-3420.
6. D. L. Boger, R. T. Beresis, O. Loiseleur, J. H. Wu, S. L. Castle, Bioorg. Med. Chem. Lett. 1998, 8, 721-724.
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8. H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2484.
9. K. C. Nicolaou, M. Takayanagi, N. F. Jain, S. Natarajan, A. E. Koumbis, T. Bando, J. M. Ramanjulu, Angew. Chem. 1998, 110, 2881-2883; Angew. Chem. Int. Ed. 1998, 37, 2717-2719.
10. K. C. Nicolaou, M. Takayanagi, N. F. Jain, S. Natarajan, A. E. Koumbis, T. Bando, J. M. Ramanjulu, Angew. Chem. 1998, 110, 2881-2883; Angew. Chem. Int. Ed. 1998, 37, 2717-2719.