A synthesis of the C1-N12 tripeptide fragment of sanglifehrin A

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2109-2112

  Bänteli, Rolf ^a   Brun, Ivan ^a   Hall, Philip ^a   Metternich, Rainer ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPHILIN A; CYCLOSPORIN A; IMMUNOSUPPRESSIVE AGENT; SANGLIFEHRIN A; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG ISOLATION; DRUG POTENCY; DRUG SYNTHESIS; IMMUNOREGULATION; STRUCTURE ACTIVITY RELATION;

EID: 0033548671     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00212-9     Document Type: Article

References (14)

1. International Patent Publication Number: WO 97/22085.
2. Xi, N.; Alemany, L.B.; Ciufolini, M.A. J. Am. Chem. Soc., 1998, 720, 80.
3. Stille, J.K. Pure & Appl. Chem., 1985, 57, 1771.
4. Evans, D.A.; Gage, J.R.; Leighton, J. L. J. Am. Chem. Soc., 1992, 114, 9434.
5. Evans, D.A.; Britton, T.C.; Ellman, J.A.; Dorow, R.L. J. Am. Chem. Soc., 1990, 112, 4011.
6. Catalytic reduction in the absence of Boc-anhydride leads to opening of the oxazolidinone by the resultant α-amino functionality as shown. (formula presented)
7. (a) Sheehan, J.C., Ledis, S.L. J. Am. Chem. Soc., 1973, 95, 875.
8. (b) Konig, W.; Geiger, R. Chemische Berichte, 1970, 103, 788.
9. The coupling of the corresponding free base generated in situ is sufficiently rapid such that oxazolidinone ring opening (cf. Ref. 6) does not occur.
10. Evans, D.A.; Britton, T.C.; Ellman, J.A. Tetrahedron Lett., 1987, 28, 6141.
11. 13C NMR, IR and Microanalysis.
12. Hale, K.J.; Delisser, V.M.; Manaviazar, S. Tetrahedron Lett., 1992, 33, 7613.
13. 7 :- C64.41, H 7.43, N 9.39, O 18.77. Obtained:- C 64.23, H 7.49, N 9.30, O 19.06.
14. 6 :- C 58.05, H 6.96, N 12.89, O 22.09. Obtained:- C 58.09, H 6.99, N 12.93, O 22.13.