Practical synthesis of an enantiomerically pure synthon for the preparation of mevinic acid analogs

DS Karanewsky, MF Malley…

Index: Karanewsky, Donald S.; Malley, Mary F.; Gougoutas, Jack Z. Journal of Organic Chemistry, 1991 , vol. 56, # 11 p. 3744 - 3747

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Citation Number: 58

Abstract

CCb, 04: C0, Me N= O 3.1-AdNH2, hexane 10 11 a.(free acid) 1 b.(1-AdNHZ sal) and 8b in essentially quantitative yield. Although the degree of prochiral recognition is rather modest, the crystalline 3S, l'S diastereomer 8a is easily separated from the oily 3R, l'S diastereomer by simple trituration or recrystallization. Thus, acid 8a was isolated in 72% yield from anhydride 4 as a single enantiomerically pure diastereomer without chromatography. The ...