Organic letters

A concise route to dihydrobenzo [b] furans: formal total synthesis of (+)-lithospermic acid

J Fischer, GP Savage, MJ Coster

Index: Fischer, Joshua; Savage, G. Paul; Coster, Mark J. Organic Letters, 2011 , vol. 13, # 13 p. 3376 - 3379

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Citation Number: 36

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.