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    Fukuyama Group-Group Meeting Cumulative Examination

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    Fukuyama Group Meeting

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    Fukuyama Group-Group Meeting Cumulative Examination

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    brightnewworld365
    29 views2 pages
    Fukuyama Group Meeting

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    2004-1

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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
    29 views2 pages

    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 4/17/04

    1.
    Me O Me OH
    N
    NOCl hν
    Me H OH Me H O
    pyridine EtOH
    H H H H

    H H

    H. Suginome et al., J. Org. Chem., 54, 5945 (1989)

    2.
    1) CHBr3, CH2Cl2
    aq NaOH (MeCO)2, hν CO2H
    phase-transfer cat., 45% 58%
    Cl Cl C5H6
    2) MeLi (2 eq), –78 to 0 °C 3) Br2, aq NaOH HO2C
    Et2O-pentane; 1,4-dioxane, 90%

    Michl, J. et al., J. Org. Chem. 53, 4593 (1988)

    3.

    3) MgX
    Ph Ph 1) I(coll)2ClO4
    medium toluene, rt OH
    OMe
    HO membered 86%
    O O
    CH2Cl2 ring
    compound 4) Ca, NH3
    –78 °C to rt, 77 % OH
    –78 °C, 92%
    2) LAH, THF
    72%

    Y. Kita et al., J. Org. Chem., 61, 7309 (1996)


    1) BH3•THF
    4. 2) CH2=C(OMe)Me
    OH PPTS
    1) AcCl
    CO2H ? ?
    HO2C
    2) EtOH (Compound) 3) NaOEt, EtOH (Compound)
    71%
    ?
    (Name)
    1) ?
    BF3•Et2O O O 2) ? O O
    EtO2C I
    Et2O 3) ?
    100% (Conditions) K. Mori (Olean)

    PhI(OAc)2
    BzO O 1) ? BzO O I2
    OH ?
    2) ? hν (Compound)
    (Conditions) CN (tungsten lamp)
    O
    11
    S. Hatakeyama (Paeoniflorin)
    天然物の全合成, p. 161 and pp. 167-168

    5. In the late 1950s R. B. Woodward published his now classic synthesis of the alkaloid reserpine. Woodward
    utilized the reaction of 1 (eq. 1) because 3 (eq. 2) was unreactive towards the desired epimerization.

    H N H H N H
    t-BuCO2H
    N N (1)
    MeO MeO
    H O H O
    H H
    OMe OMe
    O O
    1 2

    H N H H N H
    t-BuCO2H
    OAc OAc
    N N (2)
    MeO MeO
    H H H H
    MeO2C OMe MeO2C OMe

    3 4

    A. Provide a general mechanism for the equilibration of 1 to 2. 3-D drawings are not required.

    B. Provide clear 3-D drawings of the strating materials and products (1-4). Use them to explain the observed
    divergence in reactivity.

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