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Symmetry‐Based Design for the Chemoenzymatic Synthesis of Oseltamivir (Tamiflu) from Ethyl Benzoate
Author(s) -
Sullivan Bradford,
Carrera Ignacio,
Drouin Melissa,
Hudlicky Tomas
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.200901345
Subject(s) - olefin fiber , oseltamivir , dihydroxylation , ethyl benzoate , chemistry , toluene , cycloaddition , formal synthesis , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , medicine , disease , covid-19 , pathology , infectious disease (medical specialty)
A short chemoenzymatic formal synthesis of oseltamivir from ethyl benzoate has been achieved. The key steps involve a toluene dioxygenase‐mediated dihydroxylation, hetero‐Diels–Alder cycloaddition, and generation of C4 acetamido functionality. The formal synthesis of oseltamivir is achieved in ten steps and incorporates a unique translocation of the olefin with concomitant elimination of the C2 hydroxy group (see scheme).