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A Concise Synthesis of (−)‐Oseltamivir
Author(s) -
Trost Barry M.,
Zhang Ting
Publication year - 2008
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.200800282
Subject(s) - stereoselectivity , tsuji–trost reaction , yield (engineering) , combinatorial chemistry , palladium , alkylation , chemistry , key (lock) , catalysis , computer science , organic chemistry , materials science , computer security , metallurgy
Tackling the supply problem : A short and efficient synthesis of (−)‐oseltamivir has been developed which requires eight steps from commercially available starting material and proceeds with an overall yield of 30 %. Key transformations include a novel palladium‐catalyzed asymmetric allylic alkylation reaction (Pd‐AAA, see scheme) as well as a chemo‐, regio‐, and stereoselective aziridination reaction. Phth=phthaloyl.
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