Synthesis of β-phenyl-δ,ε-unsaturated amino acids and stereoselective introduction of side chain groups into [4,3,0]-bicyclic β-turn dipeptides

Tetrahedron Letters

Volumn 44, Issue 31, 2003, Pages 5863-5866

  Gu, Xuyuan ^a   Cowell, Scott ^a   Ying, Jinfa ^a   Tang, Xuejun ^a,b   Hruby, Victor J ^a  

^a 1306 E University ^*  (United States)

^b CB Research and Development   (United States)

Author keywords

Bicyclic dipeptide; Ni(II) complex; side chain; turn mimetic; , unsaturated amino acid

Indexed keywords

AMINO ACID; DIPEPTIDE; HETEROCYCLIC COMPOUND; NICKEL;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DIASTEREOISOMER; EPIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0038492792     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01383-2     Document Type: Article

References (31)

1. For recent reviews of β-turn mimetics, see: (a) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431; (b) Halab, L.; Gosselin, F.; Lubell, W. D. Biopolymers (Pept. Sci.) 2000, 55, 101.
2. For recent reviews of β-turn mimetics, see: (a) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431; (b) Halab, L.; Gosselin, F.; Lubell, W. D. Biopolymers (Pept. Sci.) 2000, 55, 101.
3. For reviews, see: (a) Rose, R. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 109; (b) Rizo, J.; Gierasch, L.-M. Ann. Rev. Biochem. 1992, 61, 387.
4. For reviews, see: (a) Rose, R. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 109; (b) Rizo, J.; Gierasch, L.-M. Ann. Rev. Biochem. 1992, 61, 387.
5. Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 53:1997;12789.
6. Nagai U., Sata K., Nakamura R., Kato R. Tetrahedron. 49:1993;3577.
7. Nagai U., Sato K. Tetrahedron Lett. 26:1985;647.
8. Estiarte M.A., Rubiralta M., Diez A. J. Org. Chem. 65:2000;6992. and references cited therein.
9. Preissner R., Goede A., Rother K., Osterkamp F., Koert U., Froemmel C. J. Computer-Aided Molecular Design. 15:2001;811.
10. Takeuchi Y., Marshall G.R. J. Am. Chem. Soc. 120:1998;5363.
11. Hruby V.J., Al-Obeidi F., Kazmiershi W. Biochem. J. 268:1990;249.
12. Hruby V.J., Li G., Haskell-Luevano C., Shenderovich M. Biopolymers (Pept.) Sci. 43:1997;219.
13. The stereochemistry of this designed bicyclic 2 is one of sixteen possible diastereomers, which provide all the predetermined topographies for bicyclic β-turn mimetics.
14. . Gu X., Tang X., Cowell S., Ying J., Hruby V.J. Tetrahedron Lett. 43:2002;6669.
15. Xiong C., Wang W., Cai C., Hruby V.J. J. Org. Chem. 67:2002;1399.
16. Xiong C., Wang W., Hruby V.J. J. Org. Chem. 67:2002;3514.
17. Rutjes F.P.J.T., Wolf L.B., Schoemaker H.E. J. Chem. Soc., Perkin Trans. 1. 2000;4197.
18. Reetx M.T. Chem. Rev. 99:1999;1121.
19. Hoffmann T., Lanig H., Waibel R., Gmeiner P. Angew. Chem., Int. Ed. Engl. 40:2001;3361.
20. Reichwein J.F., Liskamp R.M. J. Eur. J. Org. Chem. 2000;2335.
21. Belokon Y.N., Maleyev V.I., Vitt S.V., Ryzhov M.G., Kondrashov Y.D., Golubev S.N., Vauchskii Y.P., Kazika A.I., Novikova M.I., Krasutskii P.A., Yurchenko A.G., Dubochak I.L., Shklover V.E., Struchkov Y.T., Bakhmutov V.M. J. Chem. Soc., Dalton Trans. 1985;17.
22. Collet S., Carreaux F., Boucher J.-L., Pethe S., Lepoivre M., Danion-Bougot R., Danion D. J. Chem. Soc., Perkin Trans. 1. 2000;177.
23. Collet S., Bauchat P., Danion-Bougot R., Danion D. Tetrahedron: Asymmetry. 9:1998;2121.
24. 22.
25. The racemic secondary bromide 6 can be synthesized in two steps from commercially available products, See: Pandey, G.; Reddy, G. D.; Kumaraswamy, G. Tetrahedron 1994, 50, 8185.
26. Soloshonok V.A., Tang X., Hruby V.J., Meervelt L.V. Org. Lett. 3:2001;341.
27. Cai C., Soloshonok V.A., Hruby V.J. J. Org. Chem. 66:2001;1339. and references cited therein.
28. We have obtained X-ray structures of the diastereomeric cocrystal with 1/1 mixture of the S(2S,3S)/S(2R,3R) compounds, and the X-ray structure of the pure S(2R,3R)-compound which has two different conformers in the unit cell. These results will be published elsewhere.
29. b proton signal moves toward highfield, and as a result, overlap with other aromatic proton signals.
30. f value to 8 [S(2S,3S)] (0.62 for 8 [S(2S,3S)] and 0.59 for 9 [S(2S,3R)] in 1/1 hexane/acetone solution), always coexisted in the mother liquor with the major product. A small amount of 7 and 8 were purified on an analytical HPLC column (IBM silica 2872053 column with a flow of 1 mL/min, gradient elute 2∼4% isopropanol in DCM in 22 min) for characterization
31. Morell J.L., Fleckenstein P., Gross E. J. Org. Chem. 42:1977;355.