| Title | Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines |
| Authors | Zheng, Nan Chang, Yuan-Yuan Zhang, Li-Jie Gong, Jian-Xian Yang, Zhen |
| Affiliation | Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China. Peking Univ, Peking Tsinghua Ctr Life Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China. Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China. Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Chinese Minist Educ, 5 Yushan Rd, Qingdao 266003, Peoples R China. Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China. Yang, Z (reprint author), Peking Univ, Peking Tsinghua Ctr Life Sci, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China. Yang, Z (reprint author), Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China. Yang, Z (reprint author), Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Chinese Minist Educ, 5 Yushan Rd, Qingdao 266003, Peoples R China. |
| Keywords | 1 5-hydride shif cyclizationt diastereoselectivity gold spirocyclic pyrrolidinoindoline ENANTIOSELECTIVE TOTAL-SYNTHESIS ASPIDOSPERMA ALKALOIDS 2+2+2 CYCLOADDITIONS EFFICIENT SYNTHESIS HIGHLY EFFICIENT DERIVATIVES STRATEGY ROUTE (+/-)-VINCADIFFORMINE (+)-ASPIDOSPERMIDINE |
| Issue Date | 2016 |
| Publisher | CHEMISTRY-AN ASIAN JOURNAL |
| Citation | CHEMISTRY-AN ASIAN JOURNAL.2016,11,(3,SI),371-375. |
| Abstract | A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3Et2O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions. |
| URI | http://hdl.handle.net/20.500.11897/418053 |
| ISSN | 1861-4728 |
| DOI | 10.1002/asia.201500865 |
| Indexed | SCI(E) EI PubMed |
| Appears in Collections: | å å¦ä¸ å å å·¥ç¨ å¦é ¢ 化学生物学与生物技术学院 生物有机与分子工程教育部重点实验室 |
