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Asymmetric Synthesis of (+)-(11R,12S)-Mefloquine Hydrochloride

✍ Scribed by Zhi-Xiang XIE; Lu-Zhong ZHANG; Xiao-Juan REN; Shi-Yang TANG; Ying LI

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
89 KB
Volume
26
Category
Article
ISSN
0256-7660

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✦ Synopsis

Abstract

The asymmetric synthesis of (+)‐(11__R__,12__S__)‐mefloquine hydrochloride, an antimalarial drug, was accomplished from commercially available 2‐trifluoromethylaniline, ethyl 4,4,4‐trifluoroacetoacetate and cyclopentanone in 7 steps with a 14% overall yield. The key steps were proline‐catalyzed asymmetric direct aldol reaction and Beckmann rearrangement. The absolute configuration was assigned by a Mosher's method.

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