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    Fukuyama Group - Group Meeting Problems 03/06/2002: N Me H PH

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    Nguyễn Ngô Đức

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    Fukuyama Group - Group Meeting Problems 03/06/2002: N Me H PH

    Uploaded by

    Nguyễn Ngô Đức
    3 views2 pages

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    p0203

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    3 views2 pages

    Fukuyama Group - Group Meeting Problems 03/06/2002: N Me H PH

    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

    03/06/2002

    1
    O TBSOTf (2.1 eq) O
    collidine (4.2 eq)
    CH3 CH3
    CH3(CH2)14 N CH3(CH2)14 N
    CH2Cl2
    OCH3 rt, 3 hr OTBS
    61%

    2 HCOOH
    O paraformaldehyde
    CN
    NH2
    CH3CN
    reflux, 12 hr
    85%

    3 Me [(COD)RhCl]2
    O
    OEt N
    (OC)5W O Ph H
    Tungsten-carbene N Ph
    complex Ph
    pentane, 20 °C THF-EtOH (5:1) Me
    Ph 93% 20 °C, 69%
    OEt

    4
    MeO 1) m-CPBA (1.1 eq)
    CH2Cl2, rt, 3 hr CHO
    N
    H 82% CO2Me
    N
    H
    2) NaOH, MeOH HO
    N
    N rt, 5 min, 71%
    MeO2C Cl 3) TFA, CH2Cl2
    rt, 15 hr, 52%

    1) Li Cl
    O
    S
    2) HgCl2, H2O
    Fukuyama Group - Group Meeting Problems
    03/20/2002

    1 Cp2TiCl2; OTIPS
    MeMgBr, 1) BnNH2, Pd2(dba)3, P(o-tolyl) 3
    OTIPS ; NaOt-Bu

    MgBr Br2 (2 eq) 2) Pd-C, HCO2NH4, MeOH N


    reflux H
    Me Me

    t-Bu
    N 1) NaBH4, MeOH
    O
    0 °C
    2 O
    Cu
    N 2) NaH, BnBr, DMF
    Me t-Bu
    Pentacyclic 0-23 °C Me
    compound
    COCN2CO2t-Bu toluene 3) DIBAL, CH2Cl2
    O reflux –10 °C OBn
    O
    4) Tf2O, 2,6-lutidine
    ( racemic ) CH2Cl2, –78 °C

    3 O
    NBS, TMSN3 heat in toluene O Ph
    COPh N
    MeO2C
    PPh3 MeO2C Br

    O
    4 CO2Et Ti(Oi-Pr)4 1) FeCl3
    2 i-PrMgCl 2) AcONa
    C12H24O2Si
    TBSO Et2O TBSO

    1) 30% aq HCl
    5 N Cl cat. Cu(bpy)Cl reflux, 18 h
    "Olefin" N
    CO2Me ClCH2CH2Cl 2) pH 13
    reflux, 48 h

    66%

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