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    The document describes a novel and efficient synthetic route for carbocyclic nucleosides developed by Ok Hyun Ko and Joon Hee Hong using a sequential Claisen rearrangement and ring-closing metathesis. Their method involves a Johnson orthoester–Claisen rearrangement followed by ring-closing metathesis to form the key intermediate, which is then used in a palladium-catalyzed reaction to synthesize the target carbocyclic nucleosides. This 10 step synthesis route provides a new approach for producing carbocyclic nucleosides starting from simple starting materials.

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    Nhóm-6.Tổng-hợp-Hoá-dược-nè

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    The document describes a novel and efficient synthetic route for carbocyclic nucleosides developed by Ok Hyun Ko and Joon Hee Hong using a sequential Claisen rearrangement and ring-closing metathesis. Their method involves a Johnson orthoester–Claisen rearrangement followed by ring-closing metathesis to form the key intermediate, which is then used in a palladium-catalyzed reaction to synthesize the target carbocyclic nucleosides. This 10 step synthesis route provides a new approach for producing carbocyclic nucleosides starting from simple starting materials.

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    5 views9 pages

    Nhóm 6.tổng Hợp Hoá Dược Nè

    Uploaded by

    phucnguyenthcskg
    The document describes a novel and efficient synthetic route for carbocyclic nucleosides developed by Ok Hyun Ko and Joon Hee Hong using a sequential Claisen rearrangement and ring-closing metathesis. Their method involves a Johnson orthoester–Claisen rearrangement followed by ring-closing metathesis to form the key intermediate, which is then used in a palladium-catalyzed reaction to synthesize the target carbocyclic nucleosides. This 10 step synthesis route provides a new approach for producing carbocyclic nucleosides starting from simple starting materials.

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    of 9

    1

    Efficient synthesis of novel carbocyclic


    nucleosides via sequential Claisen
    rearrangement and ring-closing metathesis
    Ok Hyun Ko and Joon Hee
    Hong

    Scientific
    Seminar
    Student Bui Viet Phuong, Bui Thi Trieu Xuan
    Pham Thi Mai Anh, Nguyen Thi Nguyet
    Hanoi, 09th December 2020
    PART 1: INTRODUCTION 2

    I. Carbocyclic Nucleoside

    Figure 1. Nucleoside Figure 2. Carbocyclic Nucleoside


    PART 1: INTRODUCTION 3

    I. Carbocyclic Nucleoside

    Figure 3. Novel Carbocyclic


    Nucleoside
    PART 2: RETROSYNTHESIS 4
    ANALYSIS
    II. Retrosynthesis Analysis

    O. H. Ko, J. H. Hong / Tetrahedron Letters 43 (2002) 6399–6402

    Scheme 1. Retrosynthesis Analysis


    PART 3: SYNTHESIS 5

    III. Synthesis
    DIBALH

    CH2Cl2,
    -20, 2h Triethyl orthoacetate,
    Propionic Acid,
    Overnight, 130

    VinylMgBr DIBALH

    THF, -78, toluene,


    2h -78, 2h

    Grubb’s Catalyst,
    Benzene, reflux 1h
    ClCO2Et, pyridine,
    DMAP, overnight

    O. H. Ko, J. H. Hong / Tetrahedron Letters 43 (2002) 6399–6402

    Scheme 2. The synthetic route of the key intermediate 8


    PART 3: SYNTHESIS 6

    III. Synthesis

    i. Adenine1 and Cytosine2, Pd2(dba)3.CHCl3, P(O-i-Pr)3,


    NaH, THF/DMSO, reflux, overnight
    ii. TBAF,THF, rt, 3h

    O. H. Ko, J. H. Hong / Tetrahedron Letters 43 (2002) 6399–6402

    Scheme 3. The synthetic of Target nucleosides


    PART 4: Result and Conclusion 7

    III. Conclusion
    In summary, they have developed a very efficient
    synthetic route to the novel 4-C-hydroxymethyl
    substituted carbocyclic nucleosides starting from simple
    1,3-dihydroxyacetone.
    - Johnson orthoester–
    Claisen rearrangement
    - Ring-closing metathesis
    - Pd(0)-catalyzed reaction

    10 steps

    Scheme 4. The synthetic of Target nucleosides


    THANKS
    FOR
    LISTENING
    Does anyone have any
    questions?
    PART 5: Answer 9

    Butt, N. A., & Zhang, W. (2015). Chemical Society Reviews, 44(22), 7929–7967.

    Scheme 5. The palladium-catalyzed allylic alkylations

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