ChemInform Abstract: An Alternative Diastereospecific Approach to (.+-.)-Samin and 2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octane [Furanofuran] Lignans Based on the Ireland—Claisen Rearrangement of Unsaturated Oxa-macrolides.

✍ Scribed by H. M. HULL; R. G. JONES; D. W. KNIGHT

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199842230

✦ Synopsis

An Alternative Diastereospecific Approach to (±)-Samin and 2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octane [Furanofuran] Lignans Based on the Ireland-Claisen Rearrangement of Unsaturated Oxa-macrolides.

-Ireland-Claisen rearrangement of the macrolide (II) gives stereospecifically the tetrahydrofurancarboxylate (IV), which serves as a precursor for the synthesis of (±)-samin (VI) and (±)-sesamin (XI).