(3S,4R)-4-氨基-3-羟基-5-环已基戊酸的非氨基酸途径合成方法

A Non-Amino Acids -Based Approach to The Synthesis of (3S, 4R)-4-Amino-3-hydroxy-5-cyclohexylpentanoic Acid

报道了从 (S) -苹果酸出发合成 (3S,4R) - Statine类似物活化形式的改良方法 .使用 N-保护的苹果酰亚胺后 ,其随后的格氏试剂加成和脱氧还原可分别达到 95%的区域选择性和

Starting with (S)malic acid, a synthesis of (4S, 5R)4benzyloxy1tertbutyloxycarbonyl5cyclohexylmethyl2pyrrolidinone 14, the activated form of the corresponding (3S, 4R)4amino3hydroxy5cyclohexylpentanoic acid 5, was achieved. This approach was achieved via a regioselective (>95%) Grignard reagent addition to 9, followed by a transstereo selective (>95%) reduction as the key steps. This improved nonamino acids based approach provides a potentially versatile route to other (3S, 4R)statine analogues just by changing the Grignard reagents used.