Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides

✍ Scribed by Peiyuan Wang; Luigi A. Agrofoglio; M. Gary Newton; Chung K. Chu

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 216 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00898-8

✦ Synopsis

Asymmetric synthesis of L-carbocyclic nucleosides, (+)-I]-L-aristeromycin (11) and its thymine analog (12) was accomplished. The key intermediate 3 was synthesized by a regioselective conjugate addition to the enone 1 followed by DIBAL-H reduction. Coupling of 4 with heterocycle or construction of heterocyle by a linear approach gave 11 and 12. This is the first asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides.