ChemInform Abstract: Diastereoselective SmI2-Mediated Cascade Radical Cyclizations of Methylenecyclopropane Derivatives — A Synthesis of Paeonilactone B.

✍ Scribed by R. J. BOFFEY; M. SANTAGOSTINO; W. G. WHITTINGHAM; J. D. KILBURN

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 42 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199850214

✦ Synopsis

Diastereoselective SmI 2 -Mediated Cascade Radical Cyclizations of Methylenecyclopropane Derivatives -A Synthesis of Paeonilactone B. -Using the title cascade reaction from (VII) to (IX) as key step the natural product paeonilactone B (XIV) is synthesized in an efficient manner. The relative stereochemistry of (III) is determined by X-ray analysis of the corresponding p-nitrobenzoate. Mechanistical aspects are discussed. -(BOF-