A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

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...

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Bibliographic Details
Published in:Organic letters 2011-07, Vol.13 (13), p.3376-3379
Main Authors: Fischer, Joshua, Savage, G. Paul, Coster, Mark J
Format: Article
Language:English
Subjects:
Anti-HIV Agents - chemical synthesis
Benzofurans - chemical synthesis
Biological Products - chemical synthesis
Catalysis
Depsides - chemical synthesis
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201130h