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A practical diastereoselective synthesis of (−)‐bestatin
Author(s) -
Shang Suisheng,
Willems Andreas V.,
Chauhan Satendra S.
Publication year - 2018
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.3067
Subject(s) - oxazolidine , chemistry , diastereomer , sodium hydride , nitromethane , column chromatography , yield (engineering) , ether , organic chemistry , metallurgy , materials science
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‐O t Bu. The 8‐step synthesis afforded (−)‐bestatin in an overall yield of 24.7% after deprotection and ion exchange.