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Synthesis 1996; 1996(2): 219-222
DOI: 10.1055/s-1996-4197
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Enantioselective Synthesis of the Cyclopentene Segment of Queuosine

Keigo Tanaka, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81(22)2176845; E-mail c21799@cctu.cc.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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(3S,4R,5S)-3-Amino-4,5-dihydroxycyclopentene, the cyclopentene segment of queuosine found in the first position of the anticodon of +RNA,Tyr +RNA,His +RNA,Asn and +RNA,Asp has been synthesized in a stereoselective manner from (-)-3-endo-hydroxydicyclopentadiene.

queuosine - (3S,4R,5S)-3-amino-4,5-dihydroxycyclopentene - enantioselective synthesis - chiral cyclopentadienol synthon - chiral endo-3-hydroxydicyclopentadiene