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 - Université de Montpellier
Article Dans Une Revue European Journal of Organic Chemistry Année : 2012

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

Résumé

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

Domaines

Chimie organique

Dates et versions

hal-03468378 , version 1 (08-12-2021)

Identifiants

Citer

Pierre-Yves Géant, Jean Martínez, 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, 2012 (1), pp.62-65. ⟨10.1002/ejoc.201101333⟩. ⟨hal-03468378⟩
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