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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
Journal article   Peer reviewed

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

Pierre-Yves Géant, Jean Martínez and Xavier J Salom-Roig
European Journal of Organic Chemistry, Vol.2012(1), pp.62-65
01/2012
DOI: https://doi.org/10.1002/ejoc.201101333

Abstract

Alkaloids Epoxides Hydrazones Amination Total synthesis Alkaloids
A general strategy leading to the synthesis of two cis-2methyl-6-substituted piperidin-3-ols is described. syn-(2R,1ЈS)-2-(1-Dibenzylaminomethyl) epoxide (13) was used as common building block. The key step involved oxirane ring opening of 13 by the nucleophilic lithium aza-enolate of
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