The enantiospecific synthesis of an isoxazoline. A RGD mimic platelet GPIIb/IIIa antagonist

…, TD Costello, I Valvis, P Ma, S Kauffman…

Index: Zhang, Lin-Hua; Chung; Costello; Valvis; Ma; Kauffman; Ward Journal of Organic Chemistry, 1997 , vol. 62, # 8 p. 2466 - 2470

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Citation Number: 58

Abstract

A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and> 99.6% optical purity, starting from l-asparagine and 4- cyanobenzaldehyde. Hofmann reaction of N α-n-Boc-l-asparagine with iodosobenzene diacetate provides optically pure N α-n-Boc-l-α, β-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. ...