Enantioselective synthesis of carba-l-furanose precursors of carbanucleosides, using ring-closing metathesis

✍ Scribed by Isabelle Gillaizeau; Steve Charamon; Luigi A Agrofoglio

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 84 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01905-0

✦ Synopsis

Carba-L-sugars were synthesized in seven steps from known tetra-O-benzyl-D-galactopyranose (3). The synthesis of cyclopentene ring has been accomplished via a ring-closing metathesis step. Schrock's catalyst was employed on the unique diene, key intermediate ( ), to provide the cyclopentene derivative (7), a versatile intermediate for the synthesis of carbocyclic nucleosides.