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

doi:10.1016/j.tetasy.2010.04.046

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

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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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 language	English
Pages (from-to)	1771-1776
Number of pages	6
Journal	Tetrahedron: Asymmetry
Volume	21
Issue number	13-14
DOIs	https://doi.org/10.1016/j.tetasy.2010.04.046
Publication status	Published - 14 Jul 2010

Keywords

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

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
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@article{a93b2f217736415b81a2daac4f175266,

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

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.",

keywords = "IN-SITU GENERATION, ENANTIOSELECTIVE SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, CARBONYL-COMPOUNDS, DIAZO-COMPOUNDS, EPOXIDES, ALDEHYDES, ALKALOIDS, SULFIDES, DERIVATIVES",

author = "Muhammad Arshad and McGarrigle, {Eoghan M.} and Aggarwal, {Varinder K.} and {Fernandez Hernandez}, {Manuel A}",

year = "2010",

month = jul,

day = "14",

doi = "10.1016/j.tetasy.2010.04.046",

language = "English",

volume = "21",

pages = "1771--1776",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "13-14",

}

TY - JOUR

T1 - Synthesis of quinine and quinidine using sulfur ylide-mediated asymmetric epoxidation as a key step

AU - Arshad, Muhammad

AU - McGarrigle, Eoghan M.

AU - Aggarwal, Varinder K.

AU - Fernandez Hernandez, Manuel A

PY - 2010/7/14

Y1 - 2010/7/14

N2 - 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.

AB - 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.

KW - IN-SITU GENERATION

KW - ENANTIOSELECTIVE SYNTHESIS

KW - STEREOSELECTIVE-SYNTHESIS

KW - CARBONYL-COMPOUNDS

KW - DIAZO-COMPOUNDS

KW - EPOXIDES

KW - ALDEHYDES

KW - ALKALOIDS

KW - SULFIDES

KW - DERIVATIVES

U2 - 10.1016/j.tetasy.2010.04.046

DO - 10.1016/j.tetasy.2010.04.046

M3 - Article (Academic Journal)

SN - 0957-4166

VL - 21

SP - 1771

EP - 1776

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 13-14

ER -

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

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Keywords

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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