Stereoselective Synthesis of 4'-α-Alkylcarbovir Derivatives Based on an Asymmetric Synthesis or Chemoenzymatic Procedure

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概要

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• 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.

• 公益社団法人日本薬学会の論文
• 1999-09-15

著者

• Miyasaka T

  Showa Univ. Tokyo Jpn

• Kato K

  Toho Univ. Chiba Jpn

• Kato K

  Grad. Sch. Pharm. Sci. Nagoya City Univ.:okazaki Inst. Integ. Biosci. Natl. Inst. Natl. Sci.

• Kato Keisuke

  School Of Pharmaceutical Sciences Toho University

• Miyasaka Tadashi

  School Of Pharmaceutical Sciences Showa University

• Yamaguchi Kentaro

  Chemical Analysis Center Chiba University

• BABA Masanori

  Division of Antiviral Chemotherapy, Center for Chronic Viral Diseases, Faculty of Medicine, Kagoshim

• Akita Hiroyuki

  School Of Parmaceutical Sciences Toho University

• Suzuki Hisaki

  School Of Pharmaceutical Sciences Showa University

• TANAKA Hiromichi

  School of Pharmaceutical Sciences, Showa University

• Baba Masanori

  Division Of Human Retroviruses Center For Chronic Viral Diseases Faculty Of Medicine Kagoshima Unive

• Kato Keisuke

  School Of Pharmaceutical Science Toho University

• Yamaguchi Kentaro

  Chemical Analysis Center Chiba Univ. Chiba 263-8522 Jpn

• Tanaka Hiromichi

  School Of Pharmaceutical Sciences Showa University

• Kato Koichi

  Okazaki Institute For Integrative Bioscience Institute For Molecular Science

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