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The Synthesis of Two Furan‐Based Analogues of the α′,β′‐Epoxy Ketone Proteasome Inhibitor Eponemycin
Author(s) -
Bennacer Bibia,
Trubuil Dominique,
Rivalle Christian,
Grierson David S.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300400
Subject(s) - chemistry , furan , epoxide , ketone , amide , enantioselective synthesis , stereochemistry , serine , derivative (finance) , tripeptide , total synthesis , peptide , organic chemistry , catalysis , biochemistry , enzyme , financial economics , economics
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 analogue 5 of eponemycin was prepared ( de = 48 %). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003