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Keywords:

  • Alkaloids;
  • Epoxides;
  • Hydraz­ones;
  • Amination;
  • Total synthesis

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.