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A Concise Synthesis of (−)-Oseltamivir


  • We thank the National Institutes of Health (GM 033049) and the National Science Foundation for their generous support of our programs. T.Z. thanks Novartis for a graduate fellowship. Mass spectra were provided, in part, by the Mass Spectrometry Regional Center of the University of California, San Francisco. Palladium salts were generously supplied by Johnson-Matthey. We are indebted to Dr. Kiran Guthikonda, David N. Zalatan, and Prof. Justin Du Bois for valuable discussions and donation of chemicals for the aziridination step. We thank Gilead Sciences for a reference sample of Tamiflu.


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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.