Improved conversion of 6-endo-tosyloxybicyclo[2.2.2]octan-2-ones into 6-exo-acetoxy and 6-exo-benzoyloxybicyclo[2.2.2]octan-2-ones

✍ Scribed by Rinaldo Marini Bettolo; Luisa Maria Migneco; Piergiogio Moretti; Rita Scarpelli

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 37 KB
• Volume: 341
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/(sici)1521-3897(199910)341:7<687::aid-prac687>3.0.co;2-d

✦ Synopsis

The reaction conditions for the conversion of 6endo-tosyloxybicyclo[2.2.2]octan-2-one (7b) into 6-exo-acetoxy (8b) and 6-exo-benzoyloxybicyclo[2.2.2]octan-2-one (8a), respectively, were improved. Thus known 6-endo-tosyloxy-bicyclo[2.2.2]octan-2-ones (+)-(1RS,6SR,8SR,11RS)-11-[(4-toluenesulfonyl)oxy]tricyclo[6.2.2.0 1,6 ]dodecan-9-one (1a), 13-methyl-15-oxo-9β,13b-ethano-9β-podocarpan-12βyl-4-toluenesulfonate (3a), and methyl (13R)-16-oxo-13-[(4-