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 (+)?? …

…, J Martínez, XJ Salom??Roig

文献索引：Geant, Pierre-Yves; Martinez, Jean; Salom-Roig, Xavier J. European Journal of Organic Chemistry, 2012 , # 1 p. 62 - 65

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被引用次数: 3

摘要

Abstract A general strategy leading to the synthesis of two cis-2-methyl-6-substituted piperidin-3-ols is described. syn-(2R, 1′ S)-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 hydrazones 12a and 12b. Subsequent hydrazone hydrolysis and intramolecular reductive amination afforded the alkaloid (+)-deoxocassine ...