New neplanocin analogues. 10. The conversion of adenosine to neplanocin A, a carbocyclic nucleoside antibiotic with potent antiviral activity

✍ Scribed by Satoshi Niizuma; Satoshi Shuto; Akira Matsuda

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 735 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00894-6

✦ Synopsis

Synthesis of neplanocin A, a potent antiviral carbocyclic nucleoside, from adenosine was achieved. An acyclic adeninenucleoside 21, prepared from adenosine, was converted to 4'-keto acyclic derivative 27. When 27 was treated with lithiotrimethylsilyldiazomethane in THF, a C-H insertion reaction at the l'-position proceeded to give 6'-O-TBS-2',3'-O-isopropyrideneneplanocin A (29) along with its I'-epimer 30.