Synthesis of (2S, 3R)-3-amino-2-hydroxy-5-methylhexanoic acid derivatives. Application to the synthesis of amastatin, an inhibitor of aminopeptidases

DH Rich, BJ Moon, AS Boparai

文献索引：Rich, Daniel H.; Moon, Byung Jo; Boparai, Amrit S. Journal of Organic Chemistry, 1980 , vol. 45, # 12 p. 2288 - 2290

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被引用次数: 47

摘要

Methods are reported for the synthesis of optically pure derivatives of (2S, 3R)-3-amino-2- hydroxy-5-methylhexanoic acid.[(Benzyloxy) carbonyl]-D-leucine methyl ester was reduced in 95% yield with diisobutylaluminum hydride to the aldehyde which was converted via the cyanohydrin to (2RS, 3R)-3-amino-2-hydroxy-5-methylhexanoic acid (AHMHA). The mixture of diastereomers was converted to the corresponding Boc-AHMHA methyl ester ...