標題: Total Synthesis of Quebrachamine through Macrolactamization
作者: Hsu, Shih-Wen
Cheng, Hsiu-Yi
Huang, An-Chi
Ho, Tse-Lok
Hou, Duen-Ren
應用化學系
Department of Applied Chemistry
關鍵字: Total synthesis;Natural products;Alkaloids;Lactamization;Hydrogenation
公開日期: 1-五月-2014
摘要: The total synthesis of quebrachamine was achieved through the macrolactamization of cis-2-alkenylated indole 17, which was prepared by a Sonogashira reaction between indole 5b and piperidine 11 followed by cis-hydrogenation. We found that stoichiometric copper(I) iodide limited the undesired Glaser-type homocoupling of alkyne 11 that would otherwise take place during the Sonogashira coupling. This direct approach allowed the total synthesis in ten linear steps starting from commercially available chemicals. Conditions for the reduction of lactam 19 by lithium aluminiumhydride were adjustable, so that either (+/-)-quebrachamine or the analogue (+/-)-kopsiyunnanine D was prepared.
URI: http://dx.doi.org/10.1002/ejoc.201400064
http://hdl.handle.net/11536/24434
ISSN: 1434-193X
DOI: 10.1002/ejoc.201400064
期刊: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume: 2014
Issue: 15
起始頁: 3109
結束頁: 3115
顯示於類別:期刊論文


文件中的檔案:

  1. 000336377000011.pdf