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    Fukuyama Group - Group Meeting Problems 05/07/2003

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    Nguyễn Ngô Đức

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    Fukuyama Group - Group Meeting Problems 05/07/2003

    Uploaded by

    Nguyễn Ngô Đức
    10 views2 pages

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    p0305

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    © All Rights Reserved
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    10 views2 pages

    Fukuyama Group - Group Meeting Problems 05/07/2003

    Uploaded by

    Nguyễn Ngô Đức

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 2

    Fukuyama Group - Group Meeting Problems

    05/07/2003

    1
    O 1) 2,6-lutidine*, CH3CN, D, 88%
    S p-Tol 2) n-BuLi; TMSCl, quant.
    O
    H S SO2p-Tol
    3) MeLi (2 eq.); SO2, 75%

    (*used as buffer)

    2
    1) dimethyl D-(–)-tartrate, Ti(Oi-Pr)4
    t-BuOOH, CH2Cl2, –25 to –15 °C
    n-Pent OH n-Pent
    2) PPh3, NaHCO3, CCl4, reflux
    OH
    3) LDA (5 eq.), THF, –30 °C to rt

    3 1) Rh2(OAc)4, CH2Cl2
    AcO
    O reflux, 93%
    2) Et3N, CH2Cl2, 89% O
    N2
    3) Me3S(O)I, NaH, DMSO, 76%
    4) Pb(OAc)4, AcOH, benzene OAc
    reflux, 45%

    4
    1) BH3·NEt3 (1 eq : theoretical)
    diglyme, D H OH H

    2) CO (70 atm), HO OH
    THF, 150 °C
    3) aq. H2O2-NaOH H

    5
    CO2i-Pr OH
    1) LDA, THF
    –78 °C to 25 °C CO2i-Pr
    O
    2) decane, D
    180 °C
    Racemic
    Fukuyama Group - Group Meeting Problems
    05/28/2003

    1
    O O
    Me
    cyclopentadiene H
    OMe
    PhI(OAc)2 hn

    OH MeOH, rt acetone, rt O
    H H
    MeO OMe
    79%
    92%

    2
    1) O3, –78 °C
    H 94% 3) Ba(OH)2·8H2O CHO
    EtO2C
    2) BF3·OEt2; MeOH, 0 °C
    O CO2Me O O
    H allyltrimethylsilane 64% (2 steps)
    –78 °C

    3 H3O+ O
    72%
    Mg (activated) AcOEt to –10 °C

    THF –78 °C H3O+


    rt 91%
    to reflux OH

    Li+
    MgCl2 + Mg (activated)
    THF
    rt, 10 h

    4 OH 1) NaBH4 (2 eq) 3) NaOMe


    MeOH, rt MeO2C NHCOAr
    MeOH, rt
    O Ph
    Ph
    O N 2) MsCl (1 eq), Et3N 4) ArCOCl, Et3N
    H CO2Me
    CH2Cl2, –15 °C CH2Cl2, rt
    CF3

    Ar =
    CF3

    5 O

    O 1) Li , Et2O, –78 °C, 1h CsF (3-4 eq.),


    TBS TfO
    (not isolated) PhNTf2 (2-3 eq.),

    2) 0.5 eq. I2, THF, DME, 23 °C, 4 h OTf


    O
    –78 °C, 2 h, 74% 72%
    (Sealed reactor)
    O

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