Abstract
A simple one-pot procedure has been elaborated for the preparation of substituted benzofurans starting from halogenated phenols, and this method has been applied successfully to the total synthesis of dehydrotremetone, a natural product of White Snakeroot.
Highlights
In nature’s collection of biologically active heterocycles, benzo[b]furan derivatives[1,2,3,4] constitute a major group
A synthetic route leading to hydroxylated benzofurans would be of general interest
The present paper describes our efforts to extend the above mentioned strategy to the preparation of other hydroxylated benzofuran derivatives and to realize the ‘one-pot’ synthesis of dehydrotremetone (3)
Summary
In nature’s collection of biologically active heterocycles, benzo[b]furan derivatives[1,2,3,4] constitute a major group. We were unable to achieve any conversion in the Sonogashira coupling with 2methyl-1-buten-3-yne keeping the reaction mixtures for a prolonged time (120 hours) in a 40 oC oil bath.
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