Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones.
The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).
Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany.
SourceOrganic letters 14:9 2012 May 4 pg 2338-41
Pub Type(s)Journal Article
Research Support, Non-U.S. Gov't