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
2012.0

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 and a new C-6 ethyl analogue of this substance in good yields.

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