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Pierre-Yves Géant, Jean Martínez and Xavier J. Salom-Roig A Route to “all-cis” 2-Methyl-6-Substituted Piperidin-3-ol Alkaloids from syn-(2R,1′S)-2-(1-Dibenzylaminomethyl)epoxide: Rapid Total Synthesis of (+)-Deoxocassine European Journal of Organic Chemistry 2012

Version of Record online: 17 NOV 2011 | DOI: 10.1002/ejoc.201101333

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The total synthesis of (+)-deoxocassine and its new C-6 ethyl analogue is reported. The key step of this synthetic pathway involves C–C coupling between syn-(2R,1′S)-2-(1-dibenzylaminomethyl)epoxide and an aza-enolate of a hydrazone intermediate. This protocol is suitable to synthesize other “all-cis” 2-methyl-6-substituted piperidine-3-ol alkaloids.

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