Stereospecific synthesis of the amino acid, (S)-2-amino-(Z)- 3,5-hexadienoic acid

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1987-1990

  Cameron, Stuart ^a   Khambay, Bhupinder P S ^a  

^a ROTHAMSTED RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; AMINO ACID; AMINOALCOHOL; DIPEPTIDE; INSECT PROTEIN; INSECTICIDE; N,N DIMETHYLFORMAMIDE; TETRAHYDROFURAN; TRIETHANOLAMINE;

ANT; ARTICLE; BEETLE; BIOASSAY; OXIDATION; PROTEIN ISOLATION; RACEMIC MIXTURE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0032473898     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00112-9     Document Type: Article

References (16)

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2. 2. Aoyagi, Y.; Takasaki, S.; Fujihara, A.K.; Sugahara, T. Phytochemistry 1997, 46, 1095-1096.
3. 3. (a) Beaulieu, P.L.; Schiller, P.W., Tetrahedron Lett. 1988, 29, 2019-2022.;
4. (b) Meffre, P.; Gauzy, L.; Branquet, E.; Durand, P.; Goffic, F. L. Tetrahedron 1996, 52, 11215-11238.;
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6. 4. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31-33.; Garner, P.; Park, J.-M. Org. Synth. 1987, 70, 18-28.; Garner, P.; Park, J.-M. J. Org. Chem. 1987, 52, 2361-2364.
7. 4. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31-33.; Garner, P.; Park, J.-M. Org. Synth. 1987, 70, 18-28.; Garner, P.; Park, J.-M. J. Org. Chem. 1987, 52, 2361-2364.
8. 4. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31-33.; Garner, P.; Park, J.-M. Org. Synth. 1987, 70, 18-28.; Garner, P.; Park, J.-M. J. Org. Chem. 1987, 52, 2361-2364.
9. 5. Tsai, D. J. S.; Matteson, D. S. Tetrahedron Lett. 1981, 22, 2751-2752.
10. 3,4= 15.1Hz. (formula presented)
11. 7. Alami, M.; Ferri, F.; Gaslain, Y. Tetrahedron Lett. 1996, 37, 57-58
12. 8. Dr. G. Reginato, private communication.
13. 9. Blaskowich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030.; Blaskowich, M. A.; Lajoie, G. A. "Stereoselective synthesis of β-substituted-β-hyiroxy α-amino acids and β,γ-unsaturated α-amino acids from serine and threonine"; Thirteenth American Peptide Symposium, 1993, Edmonton, Alberta, Canada.
14. 9. Blaskowich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030.; Blaskowich, M. A.; Lajoie, G. A. "Stereoselective synthesis of β-substituted-β-hyiroxy α-amino acids and β,γ-unsaturated α-amino acids from serine and threonine"; Thirteenth American Peptide Symposium, 1993, Edmonton, Alberta, Canada.
15. 0C and extraction of the methyl ester 15 into ether.
16. 13C 54.8 ppm (C-2), 124.4 (C-3), 125.2 (C-6), 133.3 (C-5), 139.2 (C-4), 175.9 (C-1)