Yu Qingzhen, Guo Pan, Jian Jie, Chen Yuye, Xu Jing
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong Province, China.
Chem Commun (Camb). 2018 Jan 25;54(9):1125-1128. doi: 10.1039/c7cc08938d.
Strychnofoline is a Strychnos alkaloid that has unique spirooxindole architecture and possesses important anticancer activity. Here, we have, for the first time, reported the enantioselective synthesis of strychnofoline proceeding in only nine steps from commercially available 6-methoxytryptamine. The efficiency of the synthesis derives from the use of two sequential transformation steps in the catalytic asymmetric construction of the spiro[pyrrolidine-3,3'-oxindole] motif in a facile manner. Our route is amenable to the synthesis of other natural and synthetic analogs of bioactive spirooxindole alkaloids to access their therapeutic potential.
士的宁叶碱是一种具有独特螺环氧化吲哚结构且具有重要抗癌活性的马钱子属生物碱。在此，我们首次报道了从市售的6-甲氧基色胺出发，仅经过九步反应的对映选择性合成士的宁叶碱。该合成的效率源于在以简便方式催化不对称构建螺[吡咯烷-3,3'-氧化吲哚]基序过程中使用的两个连续转化步骤。我们的路线适用于合成生物活性螺环氧化吲哚生物碱的其他天然和合成类似物，以挖掘它们的治疗潜力。
