Yusuf Abdullah, Zhao Jiangyu, Wang Bianlin, Aibibula Paruke, Aisa Haji Akber, Huang Guozheng
Key Laboratory of Plant Resources and Chemistry in Arid Regions, and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, South Beijing Rd 40-1, Urumqi, 830011, People's Republic of China.
University of Chinese Academy of Sciences, Yuquan Rd 19 A, Beijing, 100049, People's Republic of China.
R Soc Open Sci. 2018 Mar 28;5(3):172037. doi: 10.1098/rsos.172037. eCollection 2018 Mar.
Rupestine is a guaipyridine sesquiterpene alkaloid isolated from L. The total synthesis of rupestine and its epimers was accomplished employing a Suzuki reaction to build a terminal diene moiety. The diene was further elaborated into the desired guaipyridine structure by a ring-closing metathesis reaction. Over all, rupestine and its three epimers were obtained as a mixture in a sequence of nine linear steps with 18.9% yield. Rupestine and its optically pure isomers were isolated by chiral preparative HPLC and fully characterized by H ,C NMR, HRMS, optical rotation value, and experimental and calculated electronic circular dichroism spectroscopy.
鲁佩斯汀是一种从L中分离出的愈创吡啶倍半萜生物碱。鲁佩斯汀及其差向异构体的全合成通过铃木反应构建末端二烯部分来完成。该二烯通过闭环复分解反应进一步转化为所需的愈创吡啶结构。总体而言，鲁佩斯汀及其三个差向异构体通过九个线性步骤以18.9%的产率作为混合物得到。鲁佩斯汀及其光学纯异构体通过手性制备高效液相色谱法分离，并通过氢、碳核磁共振、高分辨质谱、旋光值以及实验和计算的电子圆二色光谱进行了全面表征。
