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  • Title: Stereoselective synthesis of pyroglutamate natural product analogs from α- aminoacids and their anti-cancer evaluation.
    Author: Tekkam S, Alam MA, Just MJ, Berry SM, Johnson JL, Jonnalagadda SC, Mereddy VR.
    Journal: Anticancer Agents Med Chem; 2013 Dec; 13(10):1514-30. PubMed ID: 23848201.
    Abstract:
    Alkylation of α-amino acid derived iminoesters with Baylis-Hillman (BH) reaction template based allyl bromides/allyl acetates followed by acidic hydrolysis furnished α-methylene-β-substituted-pyroglutamates and α-alkylidene pyroglutamates respectively. Application of these methodologies has been demonstrated in the synthesis of fused [3.2.0]-γ-lactam-β-lactones. Further, substrate controlled stereoselective alkylation of L-threonine derived oxazoles with BH reaction based allyl bromides and acetates yielded optically pure α-methylene-β-substituted pyroglutamates, and α-alkylidene pyroglutamates. These methodologies have been applied in the preparation of chiral [3.2.0] heterobicyclic pyroglutamates containing hydroxyethyl side chain. All the synthesized pyroglutamates have been evaluated for their anti-cancer and enzyme proteasome inhibition activity.
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