α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: Application in the synthesis of all stereoisomers of α- methylthreonine

Tetrahedron Asymmetry

Volumn 15, Issue 4, 2004, Pages 719-724

  Avenoza, Alberto ^a   Busto, Jesús H ^a   Corzana, Francisco ^a   Peregrina, Jesús M ^a   Sucunza, David ^a   Zurbano, María M ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA AMINO ACID; ALPHA METHYLTHREONINE; BROMINE DERIVATIVE; HYDROXYAMINO ACID; MAGNESIUM DERIVATIVE; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; DRUG SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL; STEREOISOMERISM;

EID: 1042275588     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.12.001     Document Type: Article

References (24)

1. Huang Z., He Y.-B., Raynor K., Tallent M., Reisine T., Goodman M. J. Am. Chem. Soc. 114:1992;9390-9401.
2. He Y.-B., Huang Z., Raynor K., Reisine T., Goodman M. J. Am. Chem. Soc. 115:1993;8066-8072.
3. Cornille F., Slomezynska U., Smythe M.L., Beusen D.D., Moeller K.D., Marshall G.R. J. Am. Chem. Soc. 117:1995;909-917.
4. Chalmers D.K., Marshall G. J. Am. Chem. Soc. 117:1995;5927-5937.
5. Toniolo C., Crisma M., Formaggio F., Peggion C. Biopolymers (Pept. Sci.). 60:2001;396-419.
6. Goodman M., Ro S. Wolff M.E. Burger's Medicinal Chemistry and Drug Discovery, 5th. Vol. 1:1995;803-861 John Wiley & Sons, New York.
7. Shao H., Rueter J.K., Goodman M. J. Org. Chem. 63:1998;5240-5244.
8. Wormald M.R., Petrescu A.J., Pao Y.-L., Glithero A., Elliott T., Dwek R.A. Chem. Rev. 102:2002;371-386.
9. Xiong C., Wang W., Hruby V.J. J. Org. Chem. 67:2002;3514-3517.
10. Amador M., Ariza X., García J., Sevilla S. Org. Lett. 4:2002;4511-4514.
11. Avenoza A., Cativiela C., Corzana F., Peregrina J.M., Sucunza D., Zurbano M.M. Attanasi O.A., Spinelli D. Targets in Heterocyclic Systems. Vol. 6:2002;231-244 Italian Society of Chemistry. and references cited therein.
12. Avenoza A., Cativiela C., Corzana F., Peregrina J.M., Zurbano M.M. Tetrahedron: Asymmetry. 11:2000;2195-2204.
13. Avenoza A., Busto J.H., Cativiela C., Peregrina J.M., Sucunza D., Zurbano M.M. Tetrahedron: Asymmetry. 14:2003;399-405.
14. Avenoza A., Cativiela C., Corzana F., Peregrina J.M., Sucunza D., Zurbano M.M. Tetrahedron: Asymmetry. 12:2001;949-958.
15. Weber T., Aeschimann R., Maetzke T., Seebach D. Helv. Chim. Acta. 69:1986;1365-1377.
16. Moon S.-H., Ohfune Y. J. Am. Chem. Soc. 116:1994;7405-7406.
17. Goodman M., Shao H. Pure Appl. Chem. 68:1996;1303-1308.
18. Agami C., Couty F. Tetrahedron. 58:2002;2701-2724.
19. Avenoza A., Cativiela C., Corzana F., Peregrina J.M., Zurbano M.M. J. Org. Chem. 64:1999;8220-8225.
20. Agami C., Couty F., Hamon L., Venier O. J. Org. Chem. 62:1997;2106-2112.
21. Jordá-Gregori J.M., Gonzalez-Rosende M.E., Sepúlveda- Arques J., Galeazzi R., Orena M. Tetrahedron: Asymmetry. 10:1999;1135-1144.
22. Barluenga J., Gonzalez J.M., Campos P.J., Asensio G. Angew. Chem., Int. Ed. Engl. 24:1985;319-320.
23. Barluenga J., Campos P.J., Gonzalez J.M., Suarez J.L. J. Org. Chem. 56:1991;2234-2237.
24. Sheldrick, G. M. SHELXL97. Program for the refinement of crystal structures. University of Göttingen, Germany, 1997.