Abstract

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).

Links

Publisher Full Text

Authors

Gerbino DC, Augner D, Slavov N, Schmalz HG

Institution

Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany.

Source

Organic letters 14:9 2012 May 4 pg 2338-41

MeSH

Benzofurans
Benzophenones
Biological Agents
Catalysis
Dimethyl Sulfoxide
Ketones
Light
Molecular Structure

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22519905