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...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 2010-07, Vol.21 (13), p.1771-1776
Main Authors: Arshad, Muhammad, Fernández, M. Alejandro, McGarrigle, Eoghan M., Aggarwal, Varinder K.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2010.04.046