Nonproteinogenic amino acids: An efficient asymmetric synthesis of (S)-(-)-acromelobic acid and (S)-(-)-acromelobinic acid

Tetrahedron

Volumn 58, Issue 34, 2002, Pages 6951-6963

  Adamczyk, Maciej ^a   Akireddy, Srinivasa Rao ^a   Reddy, Rajarathnam E ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Acromelobic acid; Acromelobinic acid; Nonproteinogenic amino acids; Total synthesis

Indexed keywords

ACID; ACROMELOBIC ACID; ACROMELOBINIC ACID; AMINO ACID; CITRAZINIC ACID; DEHYDROAMINO ACID; ESTER DERIVATIVE; N (BENZYLOXYCARBONYL)PHOSPHONOGLYCINE TRIMETHYL ESTER; PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL PROCEDURES; GEL CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; ION EXCHANGE CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

GADUS MORHUA;

EID: 0037136368     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00670-1     Document Type: Article

References (44)

1. (a) Barrett G.C., Chemistry and Biochemistry of the Amino Acids. 1985;Chapman and Hall, London.
2. (b) Amino Acids, Peptides and Proteins. Vols. 1-22:1968-1991;The Chemical Society, Cambridge.
3. © Greenstein J.P., Wintz M. Robert E., Chemistry of the Amino Acids. Vols. 1-3:1984;Krieger, Florida.
4. (a) Begley. J. Pharm. Pharmacol. 48:1996;136.
5. (b) Cromelin D.J.A., Storm G. Eur. J. Pharm. Sci. 2:1994;17-18.
6. © McMartin C. Handb. Exp. Pharmaco. 110:1994;371.
7. (d) Kompella U.B., Lee V.H.L. Adv. Drug Delivery Rev. 8:1992;115.
8. (a) Coppala G.M., Schuster H.F. Asymmetric Synthesis: Construction of Chiral Molecules using Amino Acids. 1987;Wiley, New York.
9. (b) Hanessian S. Total Synthesis of Natural Products: The Chiron Approach. 1983;Pergamon, Oxford.
10. (a) Duthaler R.O. Tetrahedron. 50:1994;1539.
11. (b) Ohfune Y. Acc. Chem. Res. 25:1992;360.
12. © Williams R.M. Organic Chemistry Series Volume 7: Synthesis of Optically Active α-Amino Acids. 1989;Pergamon, Oxford.
13. (a) For a recent review on the kainoid amino acid chemistry see: Parsons A.F. Tetrahedron. 52:1996;4149.
14. (b) Also see Konno K., Hashimoto K., Ohfune Y., Shiramaha H., Matsumoto T. J. Am. Chem. Soc. 110:1988;4807.
15. (a) Yamano K., Hashimoto K., Shirahama H. Heterocycles. 34:1992;445.
16. (b) Yamano K., Shirahama H. Tetrahedron. 49:1993;2427.
17. The name acromelobinic acid was assigned based on its derivatization from (S)-(-)-acromelobic acid (1) and analogy between L-stizolobic acid (3) and L-stizolobinic acid (4).
18. (a) Hattori S., Komamine A. Nature. 183:1959;1116.
19. (b) Senoh S., Imamoto S., Maeno Y. Tetrahedron Lett. 1964;3441.
20. © Chilton W.S., Hsu C.P., Zdybak W.T. Phytochemistry. 13:1974;1179.
21. Baldwin J.E., Spyvee M.R., Whitehead R.C. Tetrahedron Lett. 35:1994;6575.
22. (a) Adamczyk M., Johnson D.D., Reddy R.E. Tetrahedron. 55:1999;63.
23. (b) Adamczyk M., Akireddy S.R., Reddy R.E. Tetrahedron: Asymmetry. 10:1999;3107.
24. © Adamczyk M., Johnson D.D., Reddy R.E. Tetrahedron Lett. 40:1999;8993.
25. (d) Adamczyk M., Johnson D.D., Reddy R.E. Tetrahedron: Asymmetry. 11:2000;2289.
26. (a) Adamczyk M., Johnson D.D., Reddy R.E. Angew. Chem., Int. Ed. Engl. 38:1999;3537.
27. (b) Adamczyk M., Johnson D.D., Reddy R.E. Bioorg. Med. Chem. Lett. 10:2000;269.
28. © Adamczyk M., Johnson D.D., Reddy R.E. Tetrahedron: Asymmetry. 11:2000;3063.
29. For preliminary results on the synthesis of (S)-(-)-1 and (S)-(-)-2, see: (a) Adamczyk M., Akireddy S.R., Reddy R.E. Org. Lett. 2:2000;3421.
30. (b) Adamczyk M., Akireddy S.R., Reddy R.E. Tetrahedron: Asymmetry. 12:2001;2385.
31. Schollkopf U., Groth U., Deng C. Angew. Chem., Int. Ed. Engl. 20:1981;798.
32. Adamczyk M., Akireddy S.R., Reddy R.E. Tetrahedron. 56:2000;2379.
33. Henegar K.E., Ashford S.W., Baughman T.A., Sih J.C., Gu R.-L. J. Org. Chem. 62:1997;6588.
34. (a) Noyori R. Asymmetric Catalysis in Organic Synthesis. Vol. 2:1994;Wiley, New York. pp 16-94.
35. (b) Ohkuma T., Kitamura M., Noyori R. Ojima I., Catalytic Asymmetric Hydrogenation. Vol. 1:2000;1-110 Wiley-VCH, New York.
36. (a) Cativiela C., Mayoral J.A., Melendez E., Oro L.A., Pinillos M.T., Uson R. J. Org. Chem. 49:1984;2502.
37. (b) Bozell J.J., Vogt C.E., Gozum J. J. Org. Chem. 56:1991;2584.
38. © Dobler C., Kreuzfeld H.-J., Machalik M., Krause H.W. Tetrahedron: Asymmetry. 7:1996;117.
39. (d) Jones S.W., Palmer C.F., Paul J.M., Tiffin P.D. Tetrahedron Lett. 40:1999;1211.
40. For reviews on the asymmetric hydrogenation using chiral phosphine ligands, see: Knowles W.S. Acc. Chem. Res. 16:1983;106.
41. Buyuk G., Hardegger E. Helv. Chim. Acta. 58:1975;78.
42. Moormann A.E., Yen C.H., Yu S. Synth. Commun. 17:1987;1695.
43. For a review on Sommelet reaction see: Angyal S. J. Org. React. 8:1954;197.
44. Burk M.J., Feaster J.E., Nugent W.A., Harlow R.L. J. Am. Chem. Soc. 115:1993;10125.