Stereocontrolled synthesis of (S)-γ-fluoroleucine

Synlett

Volumn , Issue 7, 2007, Pages 1083-1084

  Padmakshan, Dharshana ^a   Bennett, Simon A ^a   Otting, Gottfried ^a   Easton, Christopher J ^a,b  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b Australian Government Australian Research Council   (Australia)

Author keywords

(S) fluoroleucine; Amino acids; Halogenation; Silver fluoride; Stereoselective synthesis

Indexed keywords

AMINO ACID DERIVATIVE; GAMMA FLUOROLEUCINE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; DRUG SYNTHESIS; FLUORINATION; HALOGENATION; STEREOCHEMISTRY;

EID: 34248202056     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977420     Document Type: Article

References (24)

1. For reviews, see: (a) Neil, E.; Marsh, G. Chem. Biol. 2000, 7, 153.
2. (b) Yoder, N. C.; Kumar, K. Chem. Soc. Rev. 2002, 31, 335.
3. For a review, see: Jäckel, C.; Koksch, B. Eur. J. Org. Chem. 2005, 4483.
4. For a review, see: Walsh, C. T. Annu. Rev. Biochem. 1984, 53, 493.
5. For a review, see: Ojima, I. New Developments in the Synthesis and Medicinal Applications of Fluoroamino Acids and Peptides, In Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications; Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds.; Elsevier: Amsterdam, 1993, 241-273.
6. See, for example: (a) Tolman, V. Amino Acids 1996, 11, 15.
7. (b) Kroger, S.; Haufe, G. Amino Acids 1997, 12, 363.
8. (c) Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 2000, 17, 621.
9. (d) Qiu, X.-L.; Meng, W.-D.; Qing, F.-L. Tetrahedron 2004, 60, 6711.
10. Ozawa, K.; Dixon, N. E.; Otting, G. IUBMB Life 2005, 57, 615.
11. Feeney, J.; McCormick, J. E.; Bauer, C. J.; Birdsall, B.; Moody, C. M.; Starkmann, B. A.; Young, D. W.; Francis, P.; Havlin, R. H.; Arnold, W. D.; Oldfield, E. J. Am. Chem. Soc. 1996, 118, 8700.
12. Papageorgiou, C.; Borer, X.; French, R. R. Bioorg. Med. Chem. Lett. 1994, 4, 267.
13. Limanto, J.; Shafiee, A.; Devine, P. N.; Upadhyay, V.; Desmond, R. A.; Foster, B. R.; Gauthier, D. R. Jr.; Reamer, R. A.; Volante, R. P. J. Org. Chem. 2005, 70, 2372.
14. Truong, V. L.; Gauthier, J. Y.; Boyd, M.; Roy, B.; Scheigetz, J. Synlett 2005, 1279.
15. (a) Easton, C. J.; Hutton, C. A.; Rositano, G.; Tan, E. W. J. Org. Chem. 1991, 56, 5614.
16. (b) Easton, C. J.; Hutton, C. A.; Roselt, P. D.; Tiekink, E. R. T. Tetrahedron 1994, 50, 7327.
17. (c) Easton, C. J.; Hutton, C. A.; Merrett, M. C.; Tiekink, E. R. T. Tetrahedron 1996, 52, 7025.
18. (d) Easton, C. J. Chem. Rev. 1997, 97, 53.
19. (e) Easton, C. J.; Hutton, C. A. Synlett 1998, 457.
20. (a) Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450.
21. (b) O'Connell, J. L.; Simpson, J. S.; Dumanski, P. G.; Simpson, G. W.; Easton, C. J. Org. Biomol. Chem. 2006, 4, 2716.
22. (a) Wolman, Y.; Gallop, P. M.; Patchornik, A.; Berger, A. J. Am. Chem. Soc. 1962, 84, 1889.
23. (b) Cheung, H.T.; Blout, E. R. J. Org. Chem. 1965, 30, 315.
24. 2O): δ 177.3 (s), 100.4 (d, J = 160 Hz), 54.6 (s), 43.7 (d, J = 21 Hz), 30.2 (d, J = 24 Hz), 27.0 (d, J = 24 Hz).