• 제목/요약/키워드: Stereoselective

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Efficient Stereoselective Synthesis of (2S,3S,4S)-3,4-Dihydroxyglutamic Acid ((2S,3S,4S)-3,4-다이하이드록시글루타믹산의 효율적인 입체선택적 합성)

  • Jeon, Jongho;Shin, Nara;Lee, Jong Hyup;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • 제25권4호
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    • pp.392-395
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    • 2014

  • (2S,3S,4S)-3,4-Dihydroxyglutamic acid (DHGA), a biologically active ${\alpha},{\beta}$-dihydroxy-${\gamma}$-amino acid, was efficiently synthesized from a readily available D-serine derivative in 30% overall yield over 11 steps. The key stereoselective $OsO_4$-catalyzed dihydroxylation reaction controlled by an N-diphenylmethylene group on the amino group of ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated (Z)-ester successfully introduced the diol moiety of the intermediate 5a in 86% with more than 10 : 1 diastereomeric ration. Then it was in turn successfully converted to the desired target compound, (2S,3S,4S)-3,4-DHGA, via simple oxidation and hydrolysis in a highly stereoselective manner and a higher yield than the previous syntheses. This result strongly supports that our synthetic methodology of stereoselective $OsO_4$-catalyzed dihydroxylation should be useful in stereoselctive synthesis of various bioactive compounds with an amino diol moiety.

  • https://doi.org/10.14478/ace.2014.1045 인용 PDF KSCI