Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis
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Recent reports have highlighted the biological activity associated with a sub-family of the tetramic acid class of natural products. Despite the fact that members of this sub-family act as protein-protein interaction inhibitors of relevance to proteasome assembly, no synthetic work has been reported. This may be because this sub-family contains an unnatural 4,4-disubstitued glutamic acid, the synthesis of which provides a key challenge. Here we describe a highly stereoselective route to a masked form of this unnatural amino acid. This enabled the synthesis of two of the possible diastereomers of JBIR-22 and allowed its relative and absolute stereochemistry to be assigned.
Healy , A , Izumikawa , M , Slawin , A M Z , Shin-ya , K & Westwood , N J 2015 , ' Stereochemical assignment of the protein-protein interaction inhibitor JBIR-22 by total synthesis ' Angewandte Chemie , vol 54 , no. 13 , pp. 4046-4050 . DOI: 10.1002/anie.201411141
Copyright 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
The authors acknowledge the EPSRC and Cancer Research UK (CRUK Grant No. C21383/A6950) for funding this research.
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