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    Fukuyama Group - Group Meeting Problems 07/02/2003: Lin O Li Omom

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    Nguyễn Ngô Đức

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    Fukuyama Group - Group Meeting Problems 07/02/2003: Lin O Li Omom

    Uploaded by

    Nguyễn Ngô Đức
    7 views3 pages

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    p0307

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    7 views3 pages

    Fukuyama Group - Group Meeting Problems 07/02/2003: Lin O Li Omom

    Uploaded by

    Nguyễn Ngô Đức

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
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    Fukuyama Group - Group Meeting Problems

    07/02/2003

    1) n-BuLi (1 eq); ClCH2SCl


    1 OH
    Et2O, –78 °C to 25 °C
    A
    2) mCPBA (1 eq), CH2Cl2
    25 °C, 47% (2 steps)

    1) A, 60 °C 1) A, 60 °C

    2) t-BuOK 2) t-BuOK
    THF, 0 °C THF, 0 °C
    57% (2 steps) 85% (2 steps)

    2 OMOM
    LiN O (2 eq)
    Li O
    HO
    Br –78 °C, THF; –78 °C, THF;
    Br A
    Br isobutylaldehyde, reflux aq. HCl, ethanol, 0 °C Br

    73% 75%

    3 OH
    O
    MeO Me
    TsOH O
    O
    acetone, reflux
    HO
    n-Bu 82% n-Bu

    4
    1) PhCH2N3
    MeO OTES BF3·OEt2 O
    47%
    N
    2) Rh2(OAc)4 Ph
    90%

    5 SiEt3
    SiEt3
    H O H
    HO
    a) t-BuLi, Et2O-pentane c) Li O I O
    I –78 °C, 30 min; 0 °C, 1 h
    –78 °C

    b) Pr-C CCu, –78 °C to rt d) I2


    Fukuyama Group - Group Meeting Problems
    07/16/2003

    1 t-Bu
    1) lithium dispersion HO
    Si
    TIPSO Me t-Bu2SiCl2, THF t-Bu
    0 °C to rt OHC

    TIPSO Me
    2) O2N

    NC
    CH2Cl2, rt;
    aq. HCl/THF 56% (2steps)

    2 1) NaH; BuLi;
    I 3) hv (Pyrex) H
    O acetone/MeCN CO2Me
    CO2t-Bu 87% 0 °C
    O
    2) TFAA (2 eq) 4) p-TsOH (0.1 eq)
    TFA (25 eq) MeOH, reflux H
    acetone, 25 °C 80% in 2steps
    59%

    3
    N C N S Ph
    HO O PhH, reflux;
    O

    Ph S Ph Ph

    4 NaH, THF; 1) BnNH2


    toluene, reflux*;
    EtSCH2COCl Bn Me
    TMS OMs
    O NaI, : 73% TsOH N
    CO2Me O Me
    rt to reflux 2) NaIO4 benzene
    MeOH-H2O, rt reflux CO2Me
    87% EtS
    90%
    61%
    *Dean-Stark trap
    5
    LDA; t-Bu CHO m-CPBA
    A
    TMS THF, 61% CHCl3, 77%
    N

    380 °C
    A N
    N
    10 sec, 60% t-Bu
    O t-Bu
    O
    1.7 : 1
    Fukuyama Group - Group Meeting Problems
    07/30/2003

    1 1) TiCl4;
    OSiMe3

    SiMe3 OPh Me3Si OH


    O Me 2) TsOH Me
    BnO
    OSiPh3 CH2Cl2, –78 °C benzene, 40 °C BnO
    80% (2 steps) O O

    2 1) PhOPh
    Cbz reflux, 60 min
    N CO2Me 90% MeO2C

    2) SeO2 (2 eq) N
    HCO2H (2 eq) Cbz OH
    dioxane, 90 ºC
    4 hr, 68%

    3
    MsCl
    , BF3•Et2O Et3N DBU
    OH H O O
    CH2Cl2 CH2Cl2 benzene
    N –78 ºC, 2 h rt, 2 h 80 ºC, 70 h O
    O PMP NHPMP
    85% 74% 61 %
    racemic

    4
    O O
    1) acetylene, hn

    2) p-TsOH, benzene
    reflux

    N 1) Rh2(OAc)4 (1 mol%) Me
    N Ph
    130 °C
    O Me Ph
    Ph
    2) Me2AlCl HO Me
    Me Me

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