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  • Title: Cyclopeptide alkaloids: stereochemistry and synthesis of the precursors of discarines C and D and myrianthine A.
    Author: Mostardeiro MA, Ilha V, Dahmer J, Caro MS, Dalcol II, da Silva UF, Morel AF.
    Journal: J Nat Prod; 2013 Jul 26; 76(7):1343-50. PubMed ID: 23819826.
    Abstract:
    The stereochemistry of discarines C (1) and D (2) and myrianthine A (3), three cyclopeptide alkaloids isolated from Discaria febrifuga, was determined by a combination of NMR studies of 1-3, enantioselective gas chromatography, and comparison of NMR data with those of synthetic tripeptides. For the synthesis of peptides, the nonproteinogenic amino acid 3-phenylserine was also obtained in its four diastereoisomeric forms (l and d threo, obtained by recrystallization of the diastereoisomeric tripeptide, and l and d erythro, obtained by a Mitsunobu reaction with the threo-tripeptides). The general synthetic strategy described in this paper allows the tripeptide to be obtained with the free N-terminal extremity protected or dimethylated. This strategy also allows the synthesis of the corresponding peptide with an imidazolidinone ring.
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