Total synthesis and absolute configuration of minalemine A, a guanidine peptide from the marine tunicate Didemnum rodriguesi.

@article{Expsito2001TotalSA,
  title={Total synthesis and absolute configuration of minalemine A, a guanidine peptide from the marine tunicate Didemnum rodriguesi.},
  author={A. Exp{\'o}sito and M. Fernandez-Suarez and T. Iglesias and L. Mu{\~n}oz and R. Riguera},
  journal={The Journal of organic chemistry},
  year={2001},
  volume={66 12},
  pages={
          4206-13
        }
}
  • A. Expósito, M. Fernandez-Suarez, +2 authors R. Riguera
  • Published 2001
  • Chemistry, Medicine
  • The Journal of organic chemistry
  • The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the beta-amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical 1H… CONTINUE READING
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