Oseltamivir Total Synthesis
Oseltamivir total synthesis concerns the total synthesis of the antiinfluenza drug oseltamivir marketed by Hoffmann-La Roche under the trade name ''Tamiflu''. Its commercial production starts from the biomolecule shikimic acid harvested from Chinese star anise and from recombinant E. coli. Control of stereochemistry is important: the molecule has three stereocenters and the sought-after isomer is only 1 of 8 stereoisomers. Commercial production The current production method is based on the first scalable synthesis developed by Gilead Sciences starting from naturally occurring quinic acid or shikimic acid. Due to lower yields and the extra steps required (because of the additional dehydration), the quinic acid route was dropped in favour of the one based on shikimic acid, which received further improvements by Hoffmann-La Roche. The current industrial synthesis is summarised below: Karpf / Trussardi synthesis The current production method includes two reaction steps with potenti ...
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