Practical synthesis of a peptide deformylase (PDF) inhibitor

Y Liu, M Prashad, L Ciszewski, K Vargas…

Index: Liu, Yugang; Prashad, Mahavir; Ciszewski, Lech; Vargas, Kevin; Repic, Oljan; Blacklock, Thomas J. Organic Process Research and Development, 2008 , vol. 12, # 2 p. 183 - 191

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Citation Number: 6

Abstract

A practical chromatography-free synthesis of an N-formylated hydroxylamine peptide deformylase inhibitor LCD320 is described. A diastereoselective Michael reaction of (4 S)-3- [2-(cyclobutylmethyl)-1-oxo-2-propenyl]-4-(phenylmethyl)-2-oxazolidinone with O-benzyl hydroxylamine was used to establish the key stereogenic center. We found that traces of residual Li+ from a previous step had a great impact on the diastereoselectivity of this ...