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Two natural diarylheptanoids, 2-benzyl-5-(2-phenylethyl)furan (1) and 2-methoxy-4-{[5-(2-phenylethyl)furan-2-yl]methyl}phenol (2), were synthesized starting from 2-furaldehyde. A Wittig reaction of 2-furaldehyde with benzyltriphenylphosphonium bromide followed by reduction of the alkene C=C bond with Mg gave 2-(2-phenylethyl)furan (5). Lithiation of 5 with BuLi at -78 followed by alkylation with benzyl bromide gave natural product 1. In another approach, Friedel-Crafts acylation of compound 5 with benzoyl chloride followed by deoxygenation of the C=O group afforded 1. The natural product 2 was also synthesized by acylation of 5 with 4-acetoxy-3-methoxybenzoyl chloride (16) followed by deoxygenation and deacetylation.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI