A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid
Abstract
A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH4Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.
Journal Title
Organic Letters
Volume
13
Issue
13
Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright 2011 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol201130h.
Subject
Chemical sciences
Organic chemical synthesis