Synthesis of the four diastereoisomers of 3-thymine-1-(tbutoxycarbonyl)aminocyclopentane-1-carboxylic acid

Tetrahedron Letters

Volumn 44, Issue 4, 2003, Pages 695-698

  Howarth, Nicola M ^a   Wakelin, Laurence P G ^b   Walker, David M ^a  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Cyclic , disubstituted amino acids; Homoserine analogues; PNA

Indexed keywords

1,4 DIIODO 2 TRITYLOXYBUTANE; 3 THYMINE 1 (BUTOXYCARBONYL)AMINOCYCLOPENTANE 1 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; DIMETHYL MALATE; ESTER DERIVATIVE; MALIC ACID DERIVATIVE; N (DIPHENYLMETHYLENE)GLYCINE ETHYL ESTER; TRITYL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DIASTEREOISOMER; SYNTHESIS;

EID: 0037455033     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02696-5     Document Type: Article

References (20)

1. Nielsen P.E., Egholm M., Berg R.H., Buchardt O. Science. 254:1991;1497-1500.
2. Uhlmann E., Peyman A., Breipohl G., Will D.W. Angew. Chem., Int. Ed. 37:1998;2796-2823. and references cited therein.
3. Boffa L.C., Carpaneto E.M., Allfrey V.G. Proc. Natl. Acad. Sci. USA. 92:1995;1901-1905.
4. Boffa L.C., Morris P.L., Carpaneto E.M., Louissaunt M., Allfrey V.G. J. Biol. Chem. 271:1996;13228-13233.
5. Ishihara T., Corey D.R. J. Am. Chem. Soc. 121:1999;2012-2020.
6. Zhang X., Ishihara T., Corey D.R. Nucleic Acids Res. 28:2000;3332-3338.
7. Nielsen P.E., Egholm M. Bioorg. Med. Chem. 9:2001;2429-2434.
8. Howarth N.M., Wakelin L.P.G. J. Org. Chem. 62:1997;5441-5450.
9. Howarth, N. M.; Topham, C. M.; Nielsen, P. E.; Wakelin, L. P. G., unpublished results.
10. Hyrup B., Egholm M., Buchardt O., Nielsen P.E. Bioorg. Med. Chem. Lett. 6:1996;1083-1088.
11. Schneider K.C., Benner S.A. J. Am. Chem. Soc. 112:1990;453-455.
12. Augustyns K., Aerschot A.V., Schepdael A.V., Urbanke C., Herdewijn P. Nucleic Acids Res. 19:1991;2587-2593.
13. Vandendriessche F., Augustyns K., Aerschot A.V., Busson R., Hoogmartens J., Herdewijn P. Tetrahedron. 49:1993;7223-7238.
14. García-Echeverría C., Hüsken D., Chiesi C.S., Altmann K.-H. Bioorg. Med. Chem. Lett. 7:1997;1123-1126.
15. Ma D., Ma J., Dai L. Tetrahedron: Asymmetry. 8:1997;825-827.
16. Colin-Messager S., Girard J.-P., Rossi J.-C. Tetrahedron Lett. 33:1992;2689-2692.
17. Brown H.C., Narasimhan S. J. Org. Chem. 49:1984;3891-3898.
18. Kotha S., Kuki A. Tetrahedron Lett. 33:1992;1565-1568.
19. Cruickshank K.A., Jiricny J., Reese C.B. Tetrahedron Lett. 25:1984;681-684.
20. Schumacher K.K., Jiang J., Joullié M.M. Tetrahedron: Asymmetry. 9:1998;47-53.