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A practical diastereoselective synthesis of (-)-bestatin.

作者信息

Shang Suisheng, Willems Andreas V, Chauhan Satendra S

机构信息

Peptides International Inc., 11621 Electron Drive, Louisville, KY, 40299, USA.

出版信息

J Pept Sci. 2018 Mar;24(3). doi: 10.1002/psc.3067. Epub 2018 Feb 12.

DOI:10.1002/psc.3067
PMID:29430772
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.

摘要

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