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Synfacts 2008(9): 0895-0895
DOI: 10.1055/s-2008-1077986
DOI: 10.1055/s-2008-1077986
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (-)-Oseltamivir
Contributor(s):Philip KocienskiB. M. Trost*, T. Zhang
Stanford University, USA
A Concise Synthesis of (-)-Oseltamivir
Angew. Chem. Int. Ed. 2008, 47: 3759-3761
Stanford University, USA
A Concise Synthesis of (-)-Oseltamivir
Angew. Chem. Int. Ed. 2008, 47: 3759-3761
Further Information
Publication History
Publication Date:
22 August 2008 (online)
Key words
oseltamivir - tamiflu - aziridines - palladium - allylic substitution - nitrene
Significance
A very concise synthesis of (-)-oseltamivir (tamiflu) features a novel palladium-catalyzed asymmetric allylic alkylation reaction using a phthalimide nucleophile to directly open the racemic lactone A.
Comment
The highly diastereo- and chemoselective nitrene insertion reaction leading to aziridine F was best accomplished using phenyliodonium bis(pivalate) as the oxidant, SES-NH2 as the nitrene source, and E as the catalyst. Copper catalysts showed poor chemoselectivity and silver or gold catalysts gave low reactivity.