Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents.
Compared with 4'-oxonucleosides, there have been far fewer systematic structure-activity relationship studies on carbocyclic nucleosides as antiviral and antitumour agents. This is mainly because of the synthetic problems in preparing the carbasugars. However, the recent discovery of the ring-closing metathesis (RCM) (a powerful tool for the preparation of 5-membered carbasugar via C-C bond formation) has made it possible to synthesize the key carbasugars to a preparative scale. This review summarizes the asymmetric syntheses of carbasugars and carbocyclic nucleosides, using an RCM reaction as a key step. Furthermore, the review includes valuable information for designing and synthesizing novel carbocyclic nucleosides.
Jeong
Lak Shin
LS
Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, South Korea. lakjeong@ewha.ac.kr
Lee
Jeong A
JA
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002241:Carbohydrates / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry; D003500:Cyclization; D015224:Dideoxynucleosides / Q000138:chemical synthesis / Q000494:pharmacology; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D002241:Carbohydrates; D003432:Cross-Linking Reagents; D015224:Dideoxynucleosides; D009705:Nucleosides; C057503:carbovir