Synthesis of quinine and quinidine using sulfur ylide-mediated asymmetric epoxidation as a key step

Muhammad Arshad, Eoghan M. McGarrigle, Varinder K. Aggarwal*, Manuel A Fernandez Hernandez

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

20 Citations (Scopus)

Abstract

The epoxidation of meroquinene aldehyde with a chiral sulfur ylide as the key step in the synthesis of quinine and quinidine is described. The epoxidation reactions proceed under reagent control with high selectivity and good yield. The effect of sulfide and ylide substituents on the stereochemical outcome of the reaction is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1771-1776
Number of pages6
JournalTetrahedron: Asymmetry
Volume21
Issue number13-14
DOIs
Publication statusPublished - 14 Jul 2010

Keywords

  • IN-SITU GENERATION
  • ENANTIOSELECTIVE SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • CARBONYL-COMPOUNDS
  • DIAZO-COMPOUNDS
  • EPOXIDES
  • ALDEHYDES
  • ALKALOIDS
  • SULFIDES
  • DERIVATIVES

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