1356546-06-9Relevant academic research and scientific papers
Stereoselective divergent synthesis of 1,2-aminoalcohol-containing heterocycles from a common chiral nonracemic building block
Géant, Pierre-Yves,Grenet, Erwann,Martínez, Jean,Salom-Roig, Xavier J.
, p. 22 - 30 (2015/12/31)
γ-N,N-Dibenzylamino-β-hydroxysulfoxide 1 proved to be an excellent chiral building block for the synthesis of a range of 1,2-amino alcohol-containing heterocycles. Thus, 1 was converted into 4,5-disubstuted oxazolidin-2-one 4 and aminoepoxides 2 and 3. Aminoepoxide 2 proved to be an excellent precursor to access oxazolidin-2-one 5 and azetidin-3-ol 6. Finally, 2 was used as a key intermediate that allowed the development of a divergent strategy to access cis-2-methyl-6-substituted piperidin-3-ol alkaloids. (+)-Deoxocassine 7 and a C-6 ethyl analogue 8 were prepared to illustrate this approach and to demonstrate that this strategy should be adaptable to the production of other members of this alkaloid family.
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.
scheme or table, p. 62 - 65 (2012/02/01)
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.
