Total Synthesis of Quebrachamine through Macrolactamization

SW Hsu, HY Cheng, AC Huang, TL Ho…

Index: Hsu, Shih-Wen; Cheng, Hsiu-Yi; Huang, An-Chi; Ho, Tse-Lok; Hou, Duen-Ren European Journal of Organic Chemistry, 2014 , vol. 2014, # 15 p. 3109 - 3115

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Citation Number: 4

Abstract

Abstract 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 ...