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  • (-) - Korupensamine A (TKGP-110324) M. Uemura, K. Kamikawa: Activity

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    Percival Galahad
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    This document describes the total synthesis of (-)-korupensamine A, which has antimalarial activity. The key steps involve (A) a diastereoselective lithiation and stereoselective cross-coupling, (B) a stereoselective addition, and (C) a stereoselective addition. The synthesis involves over 15 reaction steps starting from commercially available materials to produce the target compound.

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    korupensamine-US

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    This document describes the total synthesis of (-)-korupensamine A, which has antimalarial activity. The key steps involve (A) a diastereoselective lithiation and stereoselective cross-coupling, (B) a stereoselective addition, and (C) a stereoselective addition. The synthesis involves over 15 reaction steps starting from commercially available materials to produce the target compound.

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    © All Rights Reserved
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    11 views2 pages

    (-) - Korupensamine A (TKGP-110324) M. Uemura, K. Kamikawa: Activity

    Uploaded by

    Percival Galahad
    This document describes the total synthesis of (-)-korupensamine A, which has antimalarial activity. The key steps involve (A) a diastereoselective lithiation and stereoselective cross-coupling, (B) a stereoselective addition, and (C) a stereoselective addition. The synthesis involves over 15 reaction steps starting from commercially available materials to produce the target compound.

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    © All Rights Reserved
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    of 2

    (–)-Korupensamine A (TKGP-110324) M. Uemura, K.

    Kamikawa1)-3)

    OH OMe

    Me

    HO Me

    NH

    HO Me

    Activity Antimalarial（抗マラリア活性）

    (A) diastereoselective lithiation, (B) stereoselective cross-coupling,


    Key Reactions
    (C) stereoselective addition

    MeO
    OMe
    HO CHO 1) i-PrBr 1) ?
    i-PrO O
    K2CO3 OMe TsOH
    i-PrO
    2) ? O
    2) NaH
    OH TsOH MeI
    i-PrO
    i-PrO

    MeO

    Br
    O 1) BuLi;
    Cr(CO)6 i-PrO CHO
    i-PrO ? NaBH4
    O
    Bu2O-THF 2) TiCl4
    Cr(CO)3 i-PrO Cr(CO)3
    i-PrO (A)

    OBn OMe OBn OMe OBn OMe

    Br Me
    i-PrO CH2OH B(OH)2 Me Swern oxidn Me
    i-PrO CH2OH i-PrO CHO
    ?
    Cr(CO)3 ?, MeOH
    Oi-Pr
    i-PrO Cr(CO)3 Cr(CO)3
    (B) i-PrO
    OBn OMe OBn OMe

    NaH
    1) ? Me 1) ? Me ?;
    OH OH
    2) aq HCl, THF i-PrO Me 2) TBSOTf i-PrO Me ?
    under air Et3N
    O OTBS
    (C)
    i-PrO i-PrO

    OBn OMe OBn OMe OBn OMe

    Bu3SnH
    Me ? Me 1) TBAF Me
    OC(=S)SMe
    i-PrO Me toluene,  i-PrO Me 2) ? i-PrO Me
    DEAD
    Ph3P N3
    OTBS OTBS

    i-PrO i-PrO i-PrO

    OBn OMe OBn OMe

    1) ?
    1) ? ? Me3Al
    Me Me
    2) Ac2O MeCN 2) BnBr
    i-PrO Me i-PrO Me
    pyridine K2CO3
    NHAc N

    i-PrO i-PrO Me

    OBn OMe OH OMe

    Me 1) ? Me

    i-PrO Me 2) H2 HO Me
    Pd/C
    NBn NH

    i-PrO Me HO Me

    (–)-Korupensamine A

    References:
    1) K. Kamikawa, M. Uemura, Synlett, 938 (2000)
    2) K. Kamikawa, T. Watanabe, A. Daimon, M. Uemura, Tetrahedron, 56, 2325 (2000)
    3) T. Watanabe, Y. Tanaka, R. Shoda, R. Sakamoto, K. Kamikawa, M. Uemura, J. Org. Chem., 69, 4152 (2004)

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