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2005
Amino acids
U 0400
An Efficient Synthesis of Cyclic β-Amino Acid Derivatives as β-Turn Mimetics.
Racemic, higher membered cyclic β-amino acid derivatives (VI) are synthesized for
32- 175 —
the first time from N-alkenyl amines (I) and ethyl acrylate via ring-closing metathesis
as the key step. Optically pure cyclic β-amino acids (XII) are prepared in a similar manner. The synthesis of the enantiomerically pure substrates for ring-closing metathesis,
(IX), is achieved by Evans' asymmetric allylation. The RGD β-turn mimetic incorporating the seven-membered β-amino acid ester (VIa) shows good efficacy in a platelet
aggregation inhibition test. — (YAMANAKA*, T.; OHKUBO*, M.; KATO, M.;
KAWAMURA, Y.; NISHI, A.; HOSOKAWA, T.; Synlett 2005, 4, 631-634; Med.
Chem. Res. Lab., Fujisawa Pharm. Co., Ltd., Yodogawa, Osaka 532, Japan; Eng.) —
H. Hoennerscheid
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