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A Synthesis of Tamiflu by Using a Barium‐Catalyzed Asymmetric Diels–Alder‐Type Reaction
Author(s) -
Yamatsugu Kenzo,
Yin Liang,
Kamijo Shin,
Kimura Yasuaki,
Kanai Motomu,
Shibasaki Masakatsu
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200804777
Subject(s) - catalysis , chemistry , trimethylsilyl , barium , diels–alder reaction , combinatorial chemistry , organic chemistry
In pursuit of a better route : A new catalytic asymmetric synthesis of Tamiflu was developed. The key transformation was an asymmetric Diels–Alder‐type reaction of 1 and 2 catalyzed by a barium/F 2 ‐FujiCAPO complex in the presence of a CsF co‐catalyst to construct the core of Tamiflu (see scheme; TMS=trimethylsilyl). The product was converted into Tamiflu in 11 steps on a gram scale.
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