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RESEARCH ARTICLE
Contents Vol 68(4)

Synthesis of Dichotomin A: Use of a Penicillamine-Derived Pseudoproline to Furnish Native Valine Residues

Michelle S. Y. Wong A , Deni Taleski A and Katrina A. Jolliffe A B
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A School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia.

B Corresponding author. Email: kate.jolliffe@sydney.edu.au

Australian Journal of Chemistry 68(4) 627-634 https://doi.org/10.1071/CH14569
Submitted: 15 September 2014  Accepted: 22 October 2014   Published: 22 December 2014

Abstract

The total synthesis of cyclic hexapeptide dichotomin A from linear peptide precursors containing penicillamine-derived pseudoproline residues is reported. The incorporation of a pseudoproline residue led to a faster reaction and higher head-to-tail cyclization yields in comparison to linear precursors containing the native valine residue. However, deprotection of the pseudoproline resulted in significant amounts of a by-product in which a threonine side chain had undergone dehydration, resulting in a low overall yield of the natural product.


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