Issue 7, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Regioselectivity of methylation of O-demethylangolensin [1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one]. An expedient synthesis of angolensin

Kristiina Wähälä,*a   Tuija Jokela,a   Auli Salakka,a   Seppo Kaltiaa  and  Markku Mesilaaksob  

* Corresponding authors

a Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, Finland
E-mail: Kristiina.Wahala@helsinki.fi
Fax: +358 9191 50357

b Finnish Institute for Verification of the Chemical Weapons Convention, University of Helsinki, PO Box 55, Finland
Fax: +358 9191 50357

Abstract

1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one (1), also known as 2′,4′,4″-trihydroxy-α-methyldeoxybenzoin or O-demethylangolensin (ODMA), is regioselectively 4-O-alkylated at ring B via the triphenolate anion by one equivalent of methyl iodide in DMF to give angolensin 2 in good yield. Appropriate adjustments of the substrate ∶ base ∶ electrophile ratios allow the synthesis of the regioisomer 3 or the bis(methyl ether) 4.

Graphical abstract: Regioselectivity of methylation of O-demethylangolensin [1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one]. An expedient synthesis of angolensin

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Article information

DOI
https://doi.org/10.1039/B100778P
Article type
Paper
Submitted
23 Jan 2001
Accepted
22 Feb 2001
First published
20 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 642-644

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Regioselectivity of methylation of O-demethylangolensin [1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one]. An expedient synthesis of angolensin

K. Wähälä, T. Jokela, A. Salakka, S. Kaltia and M. Mesilaakso, J. Chem. Soc., Perkin Trans. 1, 2001, 642 DOI: 10.1039/B100778P

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