Structural elucidation and a novel reductive cleavage of ribofuranosyl ring C-1 - O bond of the intramolecular C-arylation product of tri-O-benzyl-β-D-ribofuranosyl fluoride

✍ Scribed by Younosuke Araki; Eiji Mokubo; Naoki Kobayashi; Jun'ichi Nagasawa; Yoshiharu Ishido

• Book ID: 104232817
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 289 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80374-9

✦ Synopsis

Treatment of 2,3,5-tri-g-benzyl-8-B-ribofuranosyl fluoride (1) with BF3*0Et2 in CH2Cl the reaction wit 2 gave the intramolecular C-arylation product (2) formed from the 2-e-benzyl group in a 83% yield.

Catalytic transfer hydrogenolysis of 2 using HCOOH as a hydrogen donor and the following acetylation of the product gave (3S,l'S,2'R)-3-(1,2,3-triacetoxypropyl)isochroman ( 9) in a 68% total yield.

We have briefly announced a novel intramolecular C-arylation reaction of 2,3,5-tri-g-benzyl-8-B-ribofuranosyl fluoride (1).2 It was, however, difficult to determine the structure of the product from its 'H-and 13C-nmr spectra, so several related reactions and debenzylation reactions were examined to provide structural proofs.

During continued investigation, 0. R. Martin reported that the same product was formed on the treatment of l-g-acetyl-