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

Authors
Wahala, K Jokela, T Salakka, A Kaltia, S Mesilaakso, M
Citation
K. Wahala et al., Regioselectivity of methylation of O-demethylangolensin [1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one]. An expedient synthesis of angolensin, J CHEM S P1, (7), 2001, pp. 642-644
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
7
Year of publication
2001
Pages
642 - 644
Database
ISI
SICI code
1472-7781(2001):7<642:ROMOO[>2.0.ZU;2-X
Abstract
1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one (1), also known as 2',4',4 " -trihydroxy-alpha -methyldeoxybenzoin or O-demethylangolensin (OD MA), 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 yie ld. Appropriate adjustments of the substrate:base:electrophile ratios allow the synthesis of the regioisomer 3 or the bis(methyl ether) 4.