A stereocontrolled approach for the synthesis of 2,5-diaryl-3,4-disubstituted furano lignans through a highly diastereoselective aldol condensation of an ester enolate with an α-chiral center: total syntheses of (−)-talaumidin and (−)-virgatusin

✍ Scribed by Kiran Matcha; Subrata Ghosh

• Book ID: 104095254
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 119 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.03.105

✦ Synopsis

A general stereocontrolled approach for entry into a family of highly biologically active 2,5-diaryl-3,4-disubstituted furano lignans has been developed. The key step involves a diastereoselective aldol-type condensation of an ester enolate having an a-chiral center with an aromatic aldehyde. The methodology has been illustrated with the total syntheses of (À)-talaumidin and (À)-virgatusin.