caa a22 4500 445879149 CHVBK 20180317145537.0 cr unu---uuuuu 170323e20110501xx s 000 0 eng 10.1007/s11030-010-9284-z doi (NATIONALLICENCE)springer-10.1007/s11030-010-9284-z Traceless synthesis of diketopiperazine fused tetrahydro- β -carbolines on soluble polymer support [Elektronische Daten] [Kaushik Chanda, Cheng-Ting Chou, Jin-Ji Lai, Shu-Fen Lin, Gorakh Yellol, Chung-Ming Sun] The Pictet-Spengler reaction, using polyethylene glycol immobilized tryptophan ester with a variety of ketones, was achieved by refluxing condition in acidic chloroform. The linear as well as cyclic ketones were employed. All the ketones were reacted within 6-8h to furnish soluble polymer-supported tetrahydro-β-carboline in good yields. Further expansion at N-terminus of tetrahydro-β-carbolines was achieved through a reaction with chloroacetyl chloride. Finally, the 2,5-diketopiperazine skeleton was constructed over a β-carboline by amination of the resulting N-chloroacetamides and subsequent intramolecular cyclization leading to cleavage of the polymer; constitutes a traceless synthesis of tetracyclic molecular architecture. Significantly, this strategy affords a straightforward and efficient approach for the construction of biological promising molecules with high purity and good yields. Graphical Abstract: Springer Science+Business Media B.V., 2010 Pictet-Spengler reaction nationallicence Soluble polymer-supported synthesis nationallicence Polyethylene glycol nationallicence Diketopiperazine nationallicence Tetrahydro- β -carbolines nationallicence Chanda Kaushik Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut Chou Cheng-Ting Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut Lai Jin-Ji Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut Lin Shu-Fen Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut Yellol Gorakh Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut Sun Chung-Ming Laboratory of Combinatorial Drug Design, Department of Applied chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut Molecular Diversity Springer Netherlands 15/2(2011-05-01), 569-581 1381-1991 15:2<569 2011 15 11030 https://doi.org/10.1007/s11030-010-9284-z text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11030-010-9284-z text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Chanda Kaushik Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut NATIONALLICENCE 700 1- Chou Cheng-Ting Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut NATIONALLICENCE 700 1- Lai Jin-Ji Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut NATIONALLICENCE 700 1- Lin Shu-Fen Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut NATIONALLICENCE 700 1- Yellol Gorakh Department of Applied Chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut NATIONALLICENCE 700 1- Sun Chung-Ming Laboratory of Combinatorial Drug Design, Department of Applied chemistry, National Chiao-Tung University, 300-10, Hsinchu, Taiwan, ROC aut NATIONALLICENCE 773 0- Molecular Diversity Springer Netherlands 15/2(2011-05-01), 569-581 1381-1991 15:2<569 2011 15 11030 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer