Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
Org Lett. 2011 Jun 17;13(12):3118-21. doi: 10.1021/ol2010193. Epub 2011 May 26.
Mefloquine hydrochloride is an important antimalarial drug. It is currently manufactured and administered in racemic form; however there are indications regarding the biological activity of the two enantiomers that suggest the superiority of the (+)-form. The asymmetric total synthesis of the (+)-enantiomer of mefloquine hydrochloride is described. The key asymmetric transformation utilized is a novel asymmetric Darzens reaction of a chiral α-chloro-N-amino cyclic carbamate hydrazone derived from an N-amino cyclic carbamate (ACC) chiral auxiliary.
盐酸甲氟喹是一种重要的抗疟药物。目前它是以消旋体的形式制造和使用的；然而，关于两种对映异构体的生物活性的一些迹象表明，（+）-形式具有优势。本文描述了盐酸甲氟喹（+）-对映异构体的不对称全合成。所利用的关键不对称转化是一种新颖的手性α-氯-N-氨基环状碳酸酯腙的不对称 Darzens 反应，该腙是由 N-氨基环状碳酸酯（ACC）手性助剂衍生而来的。
