Journal
AUSTRALIAN JOURNAL OF CHEMISTRY
Volume 65, Issue 6, Pages 690-693Publisher
CSIRO PUBLISHING
DOI: 10.1071/CH12179
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- CSIRO's Preventative Health Flagship
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Amino acids and peptides bearing cyclic hydrocarbon side-chains are of interest in the development of a wide range of bioactive molecules. The preparation of an amino acid and a dipeptide derivative bearing an unfunctionalised cubane substituent is described. Attempts to prepare a cubylalanine derivative via the corresponding dehydroalanine were unsuccessful due to the high sensitivity of this vinyl cubane compound. Conversely, the addition of cubyllithium to a (R-S)-glyoxylate sulfinimine led to an effective synthesis of a cubylglycine derivative and a cubane-substituted dipeptide in diastereomerically pure form.
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