1356546-23-0Relevant articles and documents
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
Geant, Pierre-Yves,Martinez, Jean,Salom-Roig, Xavier J.
, p. 62 - 65 (2012)
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.