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

Article abstract of DOI:10.1016/S0040-4020(97)00894-6

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 1'-position proceeded to give 6'-O-TBS-2',3'-O-isopropyrideneneplanocin A (29) along with its 1'-epimer 30.