4.8 Article

Efficient short step synthesis of Corey's tamiflu intermediate

Journal

ORGANIC LETTERS
Volume 10, Issue 5, Pages 815-816

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol7029646

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Corey's tamiflu intermediate was synthesized from a bicyclolactam adduct obtained by base-catalyzed Diels-Alder reaction of N-nosyl-3-hydroxy-2-pyridone with ethyl acrylate. A compound that has the same array of functional groups with the Corey's intermediate was obtained in four steps from the DA adduct in 47% overall yield. The intermediate itself was also prepared efficiently by simply changing the protective group.

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