A practical synthesis of antiviral cyclopropane nucleoside A-5021

(1′ S,2′ R)-9-[[1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl]guanine (A-5021, 1) was synthesized from optically active cyclopropane lactone 2 by employing: (1) selective reduction of the ester; (2) alkylation of 2-amino-6-chloropurine; and (3) reductive opening of the lactone ring. This route elim...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 50; pp. 8845 - 8847
Main Authors Onishi, Tomoyuki, Matsuzawa, Toshihiro, Nishi, Seiichi, Tsuji, Takashi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.12.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
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Summary:(1′ S,2′ R)-9-[[1′,2′-bis(hydroxymethyl)cycloprop-1′-yl]methyl]guanine (A-5021, 1) was synthesized from optically active cyclopropane lactone 2 by employing: (1) selective reduction of the ester; (2) alkylation of 2-amino-6-chloropurine; and (3) reductive opening of the lactone ring. This route eliminates the protection steps to give 1 in a good yield and is of practical value. A practical route for synthesis of anitiviral nucleoside A-5021 was developed starting from the chiral cyclopropane-lactone carboxylic acid ester.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)01858-4