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An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.

A Bronsted acid-catalyzed acetalization/oxa-Michael cascade is used to achieve the desymmetrization of p-peroxyquinols in high yields and selectivities for a variety of aliphatic and aryl aldehydes. The mechanistic study results revealed that the reaction proceeds through a dynamic kinetic resolutio... Full description

Journal Title: Journal of the American Chemical Society August 22, 2012, Vol.134(33), pp.13554-13557
Main Author: Rubush, David M
Other Authors: Morges, Michelle A , Rose, Barbara J , Thamm, Douglas H , Rovis, Tomislav
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; DOI: 1520-5126 ; DOI: 10.1021/ja3052427
Link: http://search.proquest.com/docview/1034809756/?pq-origsite=primo
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recordid: proquest1034809756
title: An asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.
format: Article
creator:
  • Rubush, David M
  • Morges, Michelle A
  • Rose, Barbara J
  • Thamm, Douglas H
  • Rovis, Tomislav
subjects:
  • Acids–Chemistry
  • Antineoplastic Agents–Chemical Synthesis
  • Catalysis–Chemistry
  • Cell Line, Tumor–Pharmacology
  • Cell Survival–Drug Effects
  • Heterocyclic Compounds–Chemical Synthesis
  • Humans–Chemistry
  • Neoplasms–Pharmacology
  • Oxyquinoline–Drug Therapy
  • Stereoisomerism–Chemical Synthesis
  • Stereoisomerism–Chemistry
  • 1,2,4-Trioxane
  • Acids
  • Antineoplastic Agents
  • Heterocyclic Compounds
  • Oxyquinoline
ispartof: Journal of the American Chemical Society, August 22, 2012, Vol.134(33), pp.13554-13557
description: A Bronsted acid-catalyzed acetalization/oxa-Michael cascade is used to achieve the desymmetrization of p-peroxyquinols in high yields and selectivities for a variety of aliphatic and aryl aldehydes. The mechanistic study results revealed that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate and the generated derivatized 1,2,4-trioxane products exhibited potent cancer cell-growth inhibition.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; DOI: 1520-5126 ; DOI: 10.1021/ja3052427
fulltext: no_fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleAn asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.
creatorRubush, David M ; Morges, Michelle A ; Rose, Barbara J ; Thamm, Douglas H ; Rovis, Tomislav
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subjectAcids–Chemistry ; Antineoplastic Agents–Chemical Synthesis ; Catalysis–Chemistry ; Cell Line, Tumor–Pharmacology ; Cell Survival–Drug Effects ; Heterocyclic Compounds–Chemical Synthesis ; Humans–Chemistry ; Neoplasms–Pharmacology ; Oxyquinoline–Drug Therapy ; Stereoisomerism–Chemical Synthesis ; Stereoisomerism–Chemistry ; 1,2,4-Trioxane ; Acids ; Antineoplastic Agents ; Heterocyclic Compounds ; Oxyquinoline
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descriptionA Bronsted acid-catalyzed acetalization/oxa-Michael cascade is used to achieve the desymmetrization of p-peroxyquinols in high yields and selectivities for a variety of aliphatic and aryl aldehydes. The mechanistic study results revealed that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate and the generated derivatized 1,2,4-trioxane products exhibited potent cancer cell-growth inhibition.
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titleAn asymmetric synthesis of 1,2,4-trioxane anticancer agents via desymmetrization of peroxyquinols through a Brønsted acid catalysis cascade.
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