6,7-Dihydroxy-5,8-dimethoxy-2<i>H</i>-chromen-2-one

Abstract

This article presents a novel approach for synthesizing a new 5,8-dimethoxy derivative of esculetin via the selective cleavage of the methylene bridge in sabandin—naturally occurring and easily synthetically accessible methoxylated coumarin. A high selectivity is achieved by using acetoxylation of methylenedioxy group with lead tetraacetate. Natural coumarin sabandin as a starting compound was prepared in a few simple steps from 5-allyl-4,7-dimethoxybenzo[d][1,3]dioxole (apiol), which is readily available from parsley and dill seed extracts. The developed method enables an efficient and straightforward synthesis of a new derivative of esculetin with potential medicinal and therapeutic applications.

Keywords

• apiol
• sabandin
• esculetin
• lead tetraacetate