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Daphmanidin A型生物碱AB环骨架的合成研究

发表时间:2017-12-15  浏览量:583  下载量:103
全部作者: 莫秀芳,唐培
作者单位: 重庆大学药学院(创新药物研究中心)
摘 要: Daphmanidin A型生物碱是一类具有重要生理活性的虎皮楠生物碱,其具有复杂的六环稠合骨架、新颖的双环[2.2.2]辛烷环核心结构以及6~9个手性中心。本研究对Daphmanidin A型虎皮楠生物碱的AB环骨架构建进行初步探索,利用极性反转反应顺利由硝基烷11制得酰胺9,随后的酸介导关环以45%的收率得到发生关环和进一步芳香化的氧化吲哚15. 虽然没有得到期望的AB骨架二烯化合物8,但这一发现为氧化吲哚化合物的不对称合成提供了一条新思路。
关 键 词: 药物化学;虎皮楠生物碱;Daphmanidin A;极性反转;氧化吲哚
Title: Synthetic studies toward the AB ring system of Daphmanidin A type alkaloids
Author: MO Xiufang, TANG Pei
Organization: School of Pharmaceutical Sciences and Innovative Drug Research Centre, Chongqing University
Abstract: Daphmanidin A type Daphniphyllaceae alkaloids possess an complex hexacyclic system, a central bicyclo[2.2.2]octane core and 6-9 stereogenic centers, which display a remarkable range of biological activities. Herein, we describe the preliminary studies toward the AB ring system of Daphmanidin A type Daphniphyllaceae alkaloids. Using umpolung approach, amide 9 was successfully generated from nitroalkane 11. However, subsequent acid mediated ring-closure provided oxoindole 15 in 45% yield, resulting from a cyclization/aromatization procedure. Although the desired AB bicyclic system diene 8 was unsuccessfully synthesized, this strategy opened a new pathway for the asymmetric synthesis of oxoindole compounds.
Key words: medicinal chemistry; Daphniphyllaceae alkaloid; Daphmanidin A; umpolung; oxoindole
发表期数: 2017年12月第23期
引用格式: 莫秀芳,唐培. Daphmanidin A型生物碱AB环骨架的合成研究[J]. 中国科技论文在线精品论文,2017,10(23):2628-2633.
 
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