An efficient synthesis of bicyclic β-turn dipeptides via a photochemical key step

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 5987-5988

  Wessig, Pablo ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Amino acids and derivatives; Bicyclic heterocyclic compounds; Peptide analogues mimetics; Photochemistry

Indexed keywords

PEPTIDE;

ARTICLE; CHEMICAL REACTION; PEPTIDE SYNTHESIS; PHOTOCHEMISTRY; PROTEIN SECONDARY STRUCTURE; PROTEIN STRUCTURE; REACTION ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0033551672     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01249-6     Document Type: Article

References (12)

1. Nagai, U.; Sato , K. Tetrahedron Lett. 1985, 26, 647.
2. Sato, K.; Nagai, U. J. Chem. Soc. Perkin Trans. 1 1986, 1231.
3. a) Etzkorn, F. A.; Guo, T.; Lipton, M. A.; Goldberg, S. D.; Bartlett, P. A. J. Am. Chem. Soc. 1994, 116, 10412.
4. b) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1996, 61, 9437.
5. c) Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron 1993, 49, 3577.
6. d) Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1994, 59, 6147.
7. e) Hanessian, S.; McNaughtin-Smith, G. Bioorganic & Medicinal Chemistry Letters 1996, 6, 1567.
8. Lindemann, U.; Wulff-Molder, D.; Wessig, P. Tetrahedron: Asym. 1998, 9, 4459.
9. Tpftu = o-pentafluorphenyl-1,1:3,3-tetramethyluronium tetrafluoroborate. An analogous synthesis of the hexafluorophosphate was described by: Habermann, J.; Kunz, H. J. Prakt. Chem. 1998, 340, 233.
10. Lindemann, U.; Reck, G.; Wulff-Molder, D.; Wessig, P. Tetrahedron 1998, 54, 2529-2544.
11. Becker, H.G.O. (Ed.), "Einführung in Die Photochemie", Dt. Verlag der Wissenschaften, Berlin, 1991.
12. q, C(8)), 125.7, 127.5, 127.9, 128.1, 128.2, 128.3, 128.5, 136.1, 143.5 (C(Ph)), 156.4(CO), 171.4(CO), 173.0 (CO). Numbering matches that of 4, which is depicted in scheme 1