• Title/Summary/Keyword: Stereoselective synthesis

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Stereoselective Synthesis of (2S,3R)-3-Hydroxyhomoserine Lactone via anti Selective Dihydroxylation of an OBO Group-Protected Vinyl Glycine Analog ((2S,3R)-3-하이드록시호모세린락톤의 입체선택적 합성 : 바이닐글라이신 OBO Ester 유도체의 입체선택적인 이중알콜화 반응)

  • Koh, Moo-hyun;Jeon, Jongho;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • v.31 no.2
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    • pp.187-192
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    • 2020

  • (2S,3R)-3-hydroxyhomoserine lactone (HSL) has been used as a key intermediate for the synthesis of various biologically active compounds. In this study, we demonstrated an efficient synthesis of HSL via anti selective dihydroxylation of a protected vinyl glycine analog with an oxabicyclo[2.2.2]octyl orthoester (OBO) ester group. Because the acyclic conformation of the substrate was efficiently controlled by the bulky OBO ester group, a diastereoselectivity of > 10 : 1 was obtained in the dihydroxylation reaction without the use of a chiral reagent. By using this result, the target compound 1 can be obtained from commercially available N-Cbz-L-serine 2 in seven steps with an overall yeid of 34%. This result could be applied to the stereoselective synthesis of biologically active molecules containing a vicinal amino diol moiety.

  • https://doi.org/10.14478/ace.2020.1019 인용 PDF KSCI

Stereoselective Total Synthesis of (-)-Cytoxazone

  • Kim, Ji-Duck;Hoon, Jung-Young
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.179.2-179.2
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    • 2003

  • We have developed the novel one-pot synthetic method for regioselective and stereoselective N-protected amines through the reaction of various ethers with chlorosulfonyl isocyanate (CSI). Also, we found a novel technique to compare directly the stability of carbocations in the solution phase and established the stability order of the various carbocations. And we reported the cleavage of benzyl and p-methoxybenzyl protecting groups of alcohols and phenols in the presence of other functional groups using CSI. (omitted)

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