Novel synthesis of a Phe-Gly E-alkene dipeptide isostere

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5359-5362

  Kranz, Martin ^a   Kessler, Horst ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDE; PEPTIDE DERIVATIVE; PSEUDOPEPTIDE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030598002     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01108-2     Document Type: Article

References (27)

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21. 2.
22. 18a Only the formation of the E configurated diene 7 was observed.
23. 2 (273.38): calcd C 74.69, H 8.48, N 5.12; found C 74.77, H 8.56, N 5.02.
24. 19. The isomeric dienes were separated by careful silica gel flash chromatography.
25. 20. Starting from diastereomeric pure mesylate the formation of only one diastereomer of the aziridine 9 was observed. The configuration of the corresponding chiral center was not determined.
26. 21. Brown, H. C.; Liotta, R.; Kramer, G. W. J. Org. Chem. 1978, 43, 1058-1063.
27. 22. Boc-Ala ψ(E-CH=CH)Gly-OH and Z-Phe ψ(E-CH=CH)Gly-OH were synthesized employing DBU. The syntheses were not optimized. The isosteres were isolated in 15% and 8% overall yield, respectively.