The Synthesis of Two Furan??Based Analogues of the α′, β′??Epoxy Ketone Proteasome Inhibitor Eponemycin

B Bennacer, D Trubuil, C Rivalle…

Index: Bennacer, Bibia; Trubuil, Dominique; Rivalle, Christian; Grierson, David S. European Journal of Organic Chemistry, 2003 , # 23 p. 4561 - 4568

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Citation Number: 11

Abstract

Abstract Myers's methodology for enantioselective amino acid synthesis was employed to prepare the N-Boc didehydroleucine amide derivative 15 and to effect its conversion into the acylfuran intermediate 17. Coupling of 19 (R= H) with N-(isooctanoyl) serine provided the furan-based analogue 4 of eponemycin (de= 96%), a peptide epoxide with potent cytotoxic and anti-angiogenesis properties. In an identical fashion the corresponding unsaturated ...

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