68779-68-0Relevant academic research and scientific papers
Stereoselective total synthesis of (±)-vindeburnol and (±)-16-epi-vindeburnol
Chen, Fener,Chen, Xiangtao,Tang, Pei,Wang, Huijing,Yu, Lei,Zhang, Wen
, p. 11669 - 11672 (2021/11/12)
A concise stereoselective total synthesis of (±)-vindeburnol and its epimer (±)-16-epi-vindeburnol is presented. This synthetic work features the utilization of Baeyer-Villiger oxidation to install different types of lactone substrate, and a sequence of a
Formal Synthesis of Bioactive Indole Alkaloids Eburnamonine, Eburnaminol, and Vindeburnol
Mondal, Pravat,Argade, Narshinha P.
, p. 1849 - 1856 (2017/04/06)
Starting from (±)-3-acetoxyglutarimide, diastereoselective formal synthesis of indole alkaloids (±)-eburnamonine, (±)-eburnaminol, and (±)-vindeburnol have been demonstrated via a common intermediate (±)-1-hydroxy-12-tosyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one in very good overall yields. The acetoxy group from (±)-3-acetoxyglutarimide was first used to induce the diastereoselectivity and also as a latent source of ketone carbonyl group. The stereoselective eliminations, reductions, and intramolecular cyclizations were the involved key steps.
Total synthesis of (±)-deethyleburnamonine and vindeburnol (RU 24722) with the corresponding nitriles as starting material
Lounasmaa, Mauri,Belle, David Din,Tolvanen, Arto
, p. 1125 - 1130 (2007/10/03)
Cyclisation occurred during base treatment of cis-nitrile (5). The resulting new imine (6) was converted into the therapeutically important deethyleburnamonine (4). Total synthesis of vindeburnol (RU 24722) (3), another important drug, was achieved in one step starting from the trans- nitrile (9).
