67010-71-3Relevant academic research and scientific papers
Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids
Lisnyak, Vladislav G.,Lynch-Colameta, Tessa,Snyder, Scott A.
supporting information, p. 15162 - 15166 (2018/10/26)
Even though there are dozens of biologically active 2-substituted and 2,6-disubstituted piperidines, only a limited number of approaches exist for their synthesis. Herein is described two Mannich-type additions to nitrones, one using β-ketoacids under catalyst-free conditions and another using methyl ketones in the presence of chiral thioureas, which can generate a broad array of such 2-substituted materials, as well as other ring variants, in the form of β-N-hydroxy-aminoketones. Both processes have broad scope, with the latter providing products with high enantioselectivity (up to 98 %). The combination of these methods, along with other critical steps, has enabled 8-step total syntheses of the 2,6-disubstituted piperidine alkaloids (?)-lobeline and (?)-sedinone.
Sedum alkaloids. V. Sedacrine, the major alkaloid of Sedum acre, and related bases
Colau, Brigitte,Hootele, Claude
, p. 470 - 472 (2007/10/02)
Sedacrine, the major alkaloid of Sedum acre, is assigned structure 5 on the basis of spectroscopic and chemical evidence.Two minor bases, sedinone 6 and dihydrosedinine 7, are described.Sedacrine 5, sedinone 6, dihydrosedinine 7, and sedinine 3 are correl
