Synthesis of arylnaphthalene lignan lactone using benzoin condensation, intramolecular thermal cyclization and Suzuki coupling

Abstract

Arylnaphthalene lactones, which are natural lignans and isolated from a wide range of plants, exhibit significant biological activity, including anticancer and antiviral activities. In this work, we have developed a versatile and convergent synthetic method for arylnaphthalene lactones, which involves the use of benzoin condensation and thermal intramolecular cyclization for preparing the key intermediate, naphthol. A high-yielding Suzuki reaction is utilized to introduce the aryl group to the C9 position of the naphthalene lactones, which allows for the construction of the arylnaphthalene lactone skeleton. (C) 2015 Elsevier Ltd. All rights reserved.