ChemInform Abstract: Total Syntheses of (.+-.)-Cyclophellitol and (1R*,6S*)-Cyclophellitol.

✍ Scribed by J. L. ACENA; O. ARJONA; J. PLUMET

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199739236

✦ Synopsis

Total Syntheses of (±)-Cyclophellitol and (1R*,6S*)-Cyclophellitol.

-(±)-Cyclophellitol (VI) is prepared starting from (I), isolated and characterized as its tetraacetyl derivative. This synthesis constitutes the shortest route developed to date with the exception of Vogel's synthesis. The unnatural isomer (XII) is also accessible via the common intermediate (VII) by a similar reaction sequence. The stereochemistry of the key step, the epoxidation of the alkenes is controlled by the nature of the hydroxyl-protecting group. This is the best way known to obtain both glycosidase inhibitors through a divergent synthetic sequence. -(ACENA,