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    Fukuyama Group-Group Meeting Cumulative Examination

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    Fukuyama Group-Group Meeting Cumulative Examination

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    brightnewworld365
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    Fukuyama Group Meeting

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    2008-1

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    Fukuyama Group Meeting

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    10 views1 page

    Fukuyama Group-Group Meeting Cumulative Examination

    Uploaded by

    brightnewworld365
    Fukuyama Group Meeting

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
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    Fukuyama Group-Group Meeting Cumulative Examination 04/19/2008

    1. Me
    Me 1) AuCl (1 mol%)
    Me Me
    CH2Cl2, 88% Me
    Me
    2) HCl, MeCN
    91% O
    OTIPS

    S. A. Kozmin et al., J. Am. Chem. Soc., 126, 11806 (2004)

    2. n-BuLi (3.0 equiv)


    TMP (3.0 equiv)
    O O EtMgBr LiCl (6.0 equiv) O
    (1.2 equiv) THF, 0 °C; TFA HO
    N N O
    THF C10H21 CH2Cl2
    I
    0 °C to rt C10H21
    OPMB
    (5.0 equiv) 96%
    88%
    –78 °C to rt

    66%, dr = 90:10
    S. P. Marsden et al., Synthesis, 3263 (2005)
    S. P. Marsden et al., J. Am. Chem. Soc., 129, 12600 (2007)

    3. fuming H2SO4
    MeCN-hexane
    0 °C to rt;
    OH
    H2O, reflux
    O NH2

    演習で学ぶ有機反応機構B例題 (化学同人)
    E. N. Jacobsen et al., Org. Synth., Coll. Vol. X 29 (2004)

    4. 1) Hg(OAc)2
    AcOH, 70-75 °C CO2Me
    + AcO
    OAc
    2) MeO2C CO2Me CO2Me
    benzene, reflux

    演習で学ぶ有機反応機構C例題 (化学同人)
    C. R. Noller and R. Dinsmore, Org. Synth., Coll. Vol. II 358 (1943)

    5.
    NCS 2) TfOCH2CO2Et 1) mCPBA
    benzene; MeCN CH2Cl2
    C11H18O2S CO2Et
    S MgBr 3) DBU, MeCN 2) C2Cl6, NaH
    0 °C DME
    THF, 0 °C
    E. Vedejs et al., J. Org. Chem., 43, 4831 (1978)
    E. Vedejs et al., J. Org. Chem., 43, 4884 (1978)

    6. Both products A and B, derived from the same starting material, are tetracyclic compounds, and B is a
    regioisomer of A. Provide the structures of A and B, and draw a reasonable arrow-pushing mechanism for
    each reaction.

    1) TMSCl
    imidazole
    OMe
    DMF OH 1) ICl, THF
    A B
    2) 140 °C 2) SmI2
    xylene THF-HMPA
    3) PPTS OAc 0 °C to rt
    MeOH
    K. Suzuki et al., Angew. Chem. Int. Ed., 45, 6294 (2006)

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