A practical diastereoselective synthesis of (−)‐bestatin |
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| Authors: | Suisheng Shang Andreas V. Willems Satendra S. Chauhan |
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| Affiliation: | Peptides International Inc., Louisville, KY, USA |
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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. |
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| Keywords: | Bestatin Nitroaldol Nef reaction (2S, 3R)‐3‐amino‐2‐hydroxy‐4‐phenylbutanoic acid diastereoselective |
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