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D-Phenylalanine derivatives 1 and 6 were utilized for the synthesis of D-Phe-ψ[(E)-CMe=CX]-D/L-Val-type EADIs as a model case in this communication. A dipeptide. D-Phe-L-Val, accommodates in the (i + 1)-(i + 2) position in the type II′ β-turn substructure of the cyclic RGD pentapeptide, cyclo(-Arg-Gly-Asp-D-Phe-Val-), previously reported: Haubner, R.; Finsinger, D.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1374.
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note
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The diastereomerically pure allyl alcohols 4a and 5a,b were readily purified by recrystallization from the diastereomixture, respectively. The syn-allyl alcohol 4b could not be isolated in this step, and thus the diastereomixture, which contained the syn-allyl alcohol 4b as a major isomer, was converted into the corresponding oxazolidin-2-one derivative 8b. The diastereomerically pure oxazolidin-2-one 8b was purified by recrystallization.
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