Total synthesis of quebrachamine through macrolactamization

Shih Wen Hsu, Hsiu Yi Cheng, An Chi Huang, Tse Lok Ho, Duen Ren Hou

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10 Scopus citations

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 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.

Original languageEnglish
Pages (from-to)3109-3115
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number15
DOIs
StatePublished - May 2014

Keywords

  • Alkaloids
  • Hydrogenation
  • Lactamization
  • Natural products
  • Total synthesis

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