Efficient synthesis of 4'-cyclopropylated carbovir analogues with use of ring-closing metathesis from glycolate.
The first synthetic route of novel 4'-cyclopropylated carbovir analgues is described. The construction of cyclopropylated quaternary carbon at 4'-position of carbocyclic nucleosides was successfully made via sequential Johnson's orthoester rearrangement and ring-closing metathesis (RCM) starting from ethyl glycolate. Synthesized compounds 15 and 16 showed moderate antiviral activity without any cytotoxicity up to 100 micromol.
Liu
Lian Jin
LJ
College of Pharmacy, Chosun University, Republic of Korea.
Yoo
Jin Cheol
JC
Hong
Joon Hee
JH
D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; C057503:carbovir