A practical diastereoselective synthesis of (−)‐bestatin
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 col...
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Veröffentlicht in: | Journal of peptide science 2018-03, Vol.24 (3), p.n/a |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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.
An 8‐step diastereoselective synthesis of (−)‐bestatin is developed via nitro‐aldol reaction in a nonpolar solvent followed by cyclization to trans‐oxazolidine in a highly diastereoselective manner (dr >16:1). |
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ISSN: | 1075-2617 1099-1387 |
DOI: | 10.1002/psc.3067 |