Regioselectivity of methylation of O-demethylangolensin [1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one]. An expedient synthesis of angolensin
Wähälä, Kristiina; Jokela, Tuija; Salakka, Auli; Kaltia, Seppo; Mesilaakso, Markku; Wähälä Kristiina; Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki; Jokela Tuija; Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki; Salakka Auli; Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki; Kaltia Seppo; Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki; Mesilaakso Markku; Finnish Institute for Verification of the Chemical Weapons Convention, University of Helsinki
Журнал:
Journal of the Chemical Society, Perkin Transactions 1
Дата:
2001
Аннотация:
1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one (1), also known as 2â ²,4â ²,4â ³-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 substrateâ â ¶â baseâ â ¶â electrophile ratios allow the synthesis of the regioisomer 3 or the bis(methyl ether) 4.
74.51Кб