首页|Catalytic[2+2+2]Tandem Cyclization with Alkyl Substituted Methylene Malonate Enabling Concise Total Synthesis of Four Malagasy Alkaloids
Catalytic[2+2+2]Tandem Cyclization with Alkyl Substituted Methylene Malonate Enabling Concise Total Synthesis of Four Malagasy Alkaloids
扫码查看
点击上方二维码区域，可以放大扫码查看
原文链接
NETL
NSTL
万方数据
维普
Myrtoidine and malagashanine,highly complex in-dole alkaloids,are effective adjuvants in developing cures for plasmodium malaria and potent multi-drug resistant agents.Despite nearly 30 years of prog-ress,myrtoidine and the related family of Malagasy alkaloids still present formidable challenges for syn-thetic chemists.Here,we developed a diastereose-lective[2+2+2]tandem cyclization reaction with alkyl-substituted methylene malonate,enabling highly efficient collective total synthesis of four Mal-agasy alkaloids from commercially available trypta-mines within 10-13 steps.The synthetic strategy included rapid and highly stereoselective assembly of the tetracyclic indoline core containing 5-7 con-tiguous stereogenic carbon centers,rarely seen in indole alkaloids.Among the four natural products,(±)-myrtoidine,(±)-11-demethoxymyrtoidine,and(±)-12-hydroxymalagashanine were synthesized for the first time,and the work on(±)-malagashanine represented the shortest synthetic route so far.Our current study should enable further explorations of chemical and biological spaces based on myrtoidine,malagashanine,and related natural products.
tandem cyclization[2+2+2]methylene malonateindole alkaloidsmyrtoidinemalagashanine
Yu-Jing Cheng、Liu-Peng Zhao、Lijia Wang、Yong Tang
展开 >
State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,University of Chinese Academy of Sciences,Shanghai 200032
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development,Shanghai Frontiers Science Center of Molecule Intelligent Syntheses,School of Chemistry and Molecular Engineering,East China Normal University,Shanghai 200062
NETL
NSTL
万方数据
维普
