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Asymmetric Synthesis of (+)‐(11 R ,12 S )‐Mefloquine Hydrochloride
Author(s) -
XIE ZhiXiang,
ZHANG LuZhong,
REN XiaoJuan,
TANG ShiYang,
LI Ying
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890231
Subject(s) - chemistry , mefloquine , aldol reaction , hydrochloride , yield (engineering) , enantioselective synthesis , stereochemistry , absolute configuration , combinatorial chemistry , catalysis , organic chemistry , plasmodium falciparum , metallurgy , materials science , malaria , immunology , biology
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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