Synthesis of Unsaturated Tryprostatin B Analogues and Determination of Their Enantiomeric Purity with (S)-1-Benzyl-6-methylpiperazine-2,5-dione

Jernej Wagger; Jurij Svete; Branko Stanovnik

doi:10.1055/s-2008-1072515

PAPER

Synthesis of Unsaturated Tryprostatin B Analogues and Determination of Their Enantiomeric Purity with (S)-1-Benzyl-6-methylpiperazine-2,5-dione

Jernej Wagger, Jurij Svete, Branko Stanovnik*
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Aškerčeva 5, P.O. Box 537, 1000 Ljubljana, Slovenia
Fax: +386(1)2419220; e-Mail: branko.stanovnik@fkkt.uni-lj.si;

Abstract

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Abstract

Novel racemic and enantiomerically enriched unsaturated tryprostatin B analogues were synthesised by an enaminone-based strategy. The synthesis also features a novel copper(I)-catalysed dipeptide formation. In addition, the enantiomeric purity of an enantiomerically enriched analogue was determined by ¹H NMR spectroscopy by use of our own chiral solvating agent.

Key words

tryprostatin B - natural product analogues - enantiomeric purity determination - chiral solvating agent - copper catalysis

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References

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