title: Efficient synthesis of 4'-cyclopropylated carbovir analogues with use of ring-closing metathesis from glycolate.
abstract: 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.
authors.affiliation: College of Pharmacy, Chosun University, Republic of Korea.
authors.forename: Lian Jin
authors.initials: LJ
authors.lastname: Liu
authors.forename: Jin Cheol
authors.initials: JC
authors.lastname: Yoo
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; C057503:carbovir