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Synthesis of Two Natural Furan‐Cyclized Diarylheptanoids via 2‐Furaldehyde
Author(s) -
Seçinti Hatice,
Seçen Hasan
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400274
Subject(s) - chemistry , deoxygenation , furan , organic chemistry , diarylheptanoids , benzyl bromide , alkylation , acylation , bromide , wittig reaction , medicinal chemistry , friedel–crafts reaction , stereochemistry , catalysis
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 CC 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, FriedelCrafts acylation of compound 5 with benzoyl chloride followed by deoxygenation of the CO 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.