Chemical and Pharmaceutical Bulletin p. 1256 - 1264 (1999)
Update date:2022-08-05
Topics:
Kato, Keisuke
Suzuki, Hisaki
Tanaka, Hiromichi
Miyasaka, Tadashi
Baba, Masanori
Yamaguchi, Kentaro
Akita, Hiroyuki
Stereoselective synthesis of 4'-α-alkylcarbovir derivatives 4 was described based on asymmetric synthesis or a chemoenzymatic procedure. The asymmetric alkylation of chiral acetal 7 gave the alkylated enol ethers 9a - c possessing a chiral quaternary carbon. The key carbocyclic intermediates 14a - c were synthesized from 9a - c via eleven-steps. Coupling of 14a - c with 2-amino-6-chloropurine followed by desilylation and subsequent hydrolysis afforded the target compounds 4a - c in moderate yield. The optically active cyclopentene intermediates 5a - c and 6a - c were also prepared by enzymatic resolution of (±)-5a - c and (±)-6a - c, respectively.
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