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Synthesis of the carbocyclic nucleoside (−)-Neplanocin A

✍ Scribed by John R Medich; Kevin B Kunnen; Carl R Johnson

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
214 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Neplanocin A has been prepared in 14 steps from cyclopentadiene (11% overall yield).

The recent attention directed at the synthesis of compounds for the treatment of viral infections has resulted in a large number of nucleoside analogues displaying antiviral activity.

Neplanocin A (NPC-A) 1, a naturally-occuring but scarce analogue of the nucleoside adenosine 2, is a compound with significant antitumor as well as antiviral activity' and has high current interest as a clinical candidate.

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New neplanocin analogues. 10. The conver
New neplanocin analogues. 10. The conversion of adenosine to neplanocin A, a carbocyclic nucleoside antibiotic with potent antiviral activity
✍ Satoshi Niizuma; Satoshi Shuto; Akira Matsuda 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 735 KB

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 t