Journal
ORGANIC LETTERS
Volume 17, Issue 3, Pages 492-495Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol503507g
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- Maurice Wilkins Centre for Molecular Biodiscovery
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The first total synthesis of YM-280193, a cyclic depsipeptide that inhibits the ADP-induced aggregation of human platelets, is described. The monomer and dipeptide fragments were prepared using conventional chemistry and subsequently assembled by Fmoc-solid-phase peptide synthesis (Fmoc-SPPS). A late-stage novel bis-alkylation-elimination of cysteine on-resin was employed to introduce the unnatural N-methyldehydroalanine moiety. The final step involved execution of a key macrolactamization reaction between the hindered unnatural N,O-dimethylthreonine and beta-hydroxyleucine residues.
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