Synthesis of enantiopure pseudo-L-vinylcyclopropyl nucleosides bearing quaternary carbon as potential anti-herpesvirus agent.
Pseudo-L-vinylcyclopropyl adenine and guanine nucleosides 11 and 12 were designed and enantiopurely synthesized starting from (S)-epichlorohydrin using tandem alkylation, regioselective oxirane-ring opening, and chemoselective reduction as key steps.
Moon
Hyung Ryong
HR
College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan, Korea. mhr108@pusan.ac.kr
Park
Ah-Young
AY
Kim
Kyung Ran
KR
Chun
Moon Woo
MW
Jeong
Lak Shin
LS
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000478:Alkylation; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D006151:Guanosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006564:Herpesviridae / Q000187:drug effects*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
D000998:Antiviral Agents; D009705:Nucleosides; D014753:Vinyl Compounds; D006151:Guanosine; D000241:Adenosine