Asymmetric synthesis of 4'-alpha-alkylcarbovir derivatives.
Asymmetric synthesis of 4'-alpha-alkylcarbovir derivatives 3 were achieved based on Sakai's asymmetric alkylation of beta-keto esters. The key carbocyclic intermediate 12 was synthesized from 6 via an eleven-step sequence. Coupling of 12 with 2-amino-6-chloropurine followed by desilylation and subsequent hydrolysis gave the target compounds 3 in moderate yields.
Kato
K
K
School of Pharmaceutical Science, Toho University, Chiba, Japan.
Suzuki
H
H
Tanaka
H
H
Miyasaka
T
T
D000478:Alkylation; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D006678:HIV / Q000187:drug effects; D007202:Indicators and Reagents; D015394:Molecular Structure; D015215:Zidovudine / Q000494:pharmacology
D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; D007202:Indicators and Reagents; C057503:carbovir; D015215:Zidovudine