Synthesis of isomeric nucleoside phosphonates: Cyclic analogs of the anti-HIV active compound, PMEA

✍ Scribed by Xiaoping Zheng; Vasu Nair

• Book ID: 104209605
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 809 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00681-x

✦ Synopsis

Synthesis of cyclic analogs of the anti-HIV active acyclic nucleoside phosphonate, PMEA, is described. A key reaction in the synthesis was the stereoselective cyclization of an acyclic phosphonyl intermediate to a phosphonyltetrahydrofuran.

Complete stereostructures of the target isomeric phosphonylnucleosides were established by COSY and NOESY NMR data and X-ray crystallographic analysis. Preliminary anti-HIV data in infected CEM-SS cells are mentioned.