A Short and Highly Stereoselective Synthesis of the 1,10-seco-Eudesmanolide Ivangulin

✍ Scribed by Priv.-Doz. Dr. Peter Metz; Dipl.-Chem. Jörn Stölting; Mechtild Läge; Prof. Dr. Bernt Krebs

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 375 KB
• Volume: 33
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.199421951

✦ Synopsis

A solution of [Ru,(CO),,] (200 mg. 0.32 mmol) and freshly distilled diazocyclopentadieiie [I31 (30 pL. 0.5 mmol) in dried T H F (40 mL) was heated at reflux under nitrogen lbi irnc hour. After evaporation of the solvent. thin-layer chromatography (SiO?) of Ihc orange-rcd residue. eluting with pentane:dichloromethane 4: 1 (v:v) gave three bands. Compound I was recovered as pale yellow crystals from hexane in 46"" yield. compound 2 as a pale yellow solid in 20% yield, and compound 4 as colorless crystals (cyclohexane) in 25 YO yield. On exposing a solution of compound 3 in T H F to sunlight for 4 h. complete conversion to 2 was achieved (IR monitoring). I : IR(C,H,,) ? ( C O