A practical diastereoselective synthesis of (−)‐bestatin

descriptionPublicationkeyboard_double_arrow_right Article 12 Feb 2018 English Publisher:WileyJournal:Journal of Peptide Science, volume 24 (issn: 1075-2617, eissn: 1099-1387,

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Authors: Suisheng Shang; Andreas V. Willems; Satendra S. Chauhan;

doi: 10.1002/psc.3067

pmid: 29430772

A practical diastereoselective synthesis of (−)‐bestatin

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Abstract

Diastereoselective addition of nitromethane to Boc‐D‐Phe‐H in the presence of sodium hydride in diethyl ether/hexane containing 15‐crown‐5 and subsequent N,O‐protection with 2,2‐dimethoxypropane gave trans‐oxazolidine in a diastereomeric ratio of >16:1. The oxazolidine was easily separated by column chromatography, which after Nef reaction was coupled to H‐Leu‐OtBu. The 8‐step synthesis afforded (−)‐bestatin in an overall yield of 24.7% after deprotection and ion exchange.

Keywords

Molecular Structure, Leucine, Stereoisomerism, Chromatography, High Pressure Liquid

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