Stereoselective synthesis of conformationally rigid apio carbanucleosides as potential antiviral agents.
Apio north-methanocarbocyclic nucleosides 1-3 with bicyclo[3. 1.0]hexane template were first synthesized. Introduction of hydroxymethyl substituent was efficiently and stereoselectively accomplished by aldol and retro-aldol reaction and fixed conformation was achieved from a modified Simmons-Smith cyclopropanation on a cyclopentane ring.
Moon
Hyung Ryong
HR
College of Pharmacy, Pusan National University, Pusan 609-735, Korea.
Kim
Kyung Ran
KR
Kim
Bum Tae
BT
Hwang
Ki Jun
KJ
Chun
Moon Woo
MW
Jeong
Lak Shin
LS
D000096:Acetone / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry*; D010420:Pentanes / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D000998:Antiviral Agents; D009705:Nucleosides; D010420:Pentanes; D011741:Pyrimidine Nucleosides; D000096:Acetone; C033353:pentane