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The Synthesis of a Cubane-Substituted Dipeptide
Quentin I.
Churches A,
Roger J.
Mulder A,
Jonathan M.
White B,
John
Tsanaktsidis A and
Peter J.
Duggan A C
A
CSIRO Materials Science and Engineering, Private Bag 10, Clayton South, Vic. 3169, Australia.
B
School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Vic. 3010, Australia.
C
Corresponding author. Email: peter.duggan@csiro.au
Australian Journal of Chemistry
65(6)
690-693 http://dx.doi.org/10.1071/CH12179
Submitted: 2 April 2012 Accepted: 2 May 2012 Published:
24
May
2012
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Abstract
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 (RS)-glyoxylate sulfinimine led to an effective synthesis of a cubylglycine derivative and a cubane-substituted dipeptide in diastereomerically pure form. 
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