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

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.

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(1S,3S,4R)-2-((2-Bromo-6-methoxyquinolin-4-yl)methyl)-3-((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)-2-thioniabicyclo[2.2.1]heptane tetrafluoroborateC26H31BBrF4NO2S[α]D24=+33 (c 1.0, CHCl3)Source of chirality: chiral sulfideAbsolute configuration: (1S,3S,4R) 3-((1S,4R)