Stereoselective synthesis of 4'-α-alkylcarbovir derivatives based on an asymmetric synthesis or chemoenzymatic procedure

DOI: 10.1248/cpb.47.1256

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1256 - 1264 (1999)

Update date:2022-08-05

Topics:

Authors:

Kato, Keisuke

Suzuki, Hisaki

Tanaka, Hiromichi

Miyasaka, Tadashi

Baba, Masanori

Yamaguchi, Kentaro

Akita, Hiroyuki

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Article abstract of DOI:10.1248/cpb.47.1256

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.