Tetrahedron Letters ( IF 1.8 ) Pub Date : 2018-12-26 , DOI: 10.1016/j.tetlet.2018.12.058 Victoria Rodríguez-Tzompanzi , Leticia Quintero , Dulce M. Tepox-Luna , Silvano Cruz-Gregorio , Fernando Sartillo-Piscil
Starting from a 1,2-O-isopropylidene-α-d-xylofuranose derivative, a non-toxic free-radical approach for the synthesis of (+)-muscarine is reported. To this end, a stereoselective allylation reaction at the anomeric position of a respective xylofuranose derivative was employed as a new synthetic strategy for the installation of the methyl group at the C-5 position of (+)-muscarine. Accordingly, the allyl group was transformed into the methyl group in three sequential steps highlighting a blue-light photoredox decarboxylation reaction. Additionally, a tin-free Barton-McCombie deoxygenation reaction of the respective C-methyl glycoside allowed the completion of this free-radical approach to (+)-muscarine.
中文翻译:
蓝光光氧化还原脱羧和无锡Barton-McCombie反应立体选择性合成(+)-毒蕈碱
从1,2 - O-异亚丙基-α- d-木呋喃糖衍生物开始,报道了合成(+)-毒蕈碱的无毒自由基方法。为此,在相应的木呋喃糖衍生物的异头位置上的立体选择性烯丙基化反应被用作将甲基安装在(+)-毒蕈碱的C-5位上的新的合成策略。因此,在三个连续步骤中,烯丙基被转化为甲基,从而突出了蓝光光氧化还原脱羧反应。另外,相应的C-甲基糖苷的无锡Barton-McCombie脱氧反应允许完成这种对(+)-毒蕈碱的自由基方法。