A concise route to dihydrobenzo[b]furans: formal total synthesis of (+)-lithospermic acid
Joshua Fischer1, G Paul Savage, Mark J Coster
1Eskitis Institute for Cell And Molecular Therapies, Griffith University, Nathan 4111 Queensland, Australia.
Abstract:
A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) 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.
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