Synthesis of Butyl 1-p-Menthene-3-A.zido-4-Hydroxy-7-Carboxylate, the Synthetic Intermediate of Statine Analogue
Hisao Shibata, Taizo Hasegawa, Hiroshi Kayahara · Institutional Repositories DataBase (IRDB) · 1988
Protease inhibitor, pepstatin is a pentapeptide which involves two unusual amino acid, statine (3S-hydroxy-4S-amino-6-methylheptanoic acid (I)). Pepstatin is known to inhibit renin in the hypertensive renin-angiotensin system and shown to suppress blood pressure strongly. The present paper deals with the simple and convenient synthesis of butyl 1-p-menthen-3-azido-4-hydroxy-7-carboxy late (III) in which III is one of the important intermediate leading to the isosteric isomer of statin, namely, p-menthan-3-amino-2-hydroxy-7-carboxylic acid (II). Further, the acid-catalysed isomerization is also discussed.