Synthesis of D- and L-apio nucleoside analogues with 2'-hydroxyl group as potential anti-HIV agents.
The present work describes the asymmetric synthesis of D- and L-apio-2',3'-dideoxynucleoside analogues, 4 and 5 with 2'-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure.
Jin
Dong Zhe
DZ
College of Pharmacy, Seoul National University, Seoul 151-742, South Korea.
Kwon
Sung Hee
SH
Moon
Hyung Ryong
HR
Gunaga
Prashantha
P
Kim
Hea Ok
HO
Kim
Dae-Kee
DK
Chun
Moon Woo
MW
Jeong
Lak Shin
LS
D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D045744:Cell Line, Tumor; D015224:Dideoxynucleosides / Q000138:chemical synthesis*; D005690:Galactose / Q000737:chemistry; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; D005690:Galactose