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    La Síntesis Total de Colesterol: R. B. Woodward

    Uploaded by

    Hector Martinez Gregorio
    1) Woodward synthesized cholesterol through a 28 step total synthesis process involving the use of reagents like sodium hydroxide, hydrochloric acid, lithium aluminum hydride, acetic anhydride, and osmium tetroxide to transform intermediates into the final product. 2) The synthesis began with commercially available starting materials that were transformed through organic reactions such as acetylation, reduction, oxidation, and alkylation to slowly construct the cholesterol molecule. 3) After 28 steps involving over a dozen organic transformations, Woodward was successfully able to synthesize cholesterol in the laboratory, achieving one of the first total syntheses of a steroid molecule.

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    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd

    La Síntesis Total de Colesterol: R. B. Woodward

    Uploaded by

    Hector Martinez Gregorio
    118 views4 pages
    1) Woodward synthesized cholesterol through a 28 step total synthesis process involving the use of reagents like sodium hydroxide, hydrochloric acid, lithium aluminum hydride, acetic anhydride, and osmium tetroxide to transform intermediates into the final product. 2) The synthesis began with commercially available starting materials that were transformed through organic reactions such as acetylation, reduction, oxidation, and alkylation to slowly construct the cholesterol molecule. 3) After 28 steps involving over a dozen organic transformations, Woodward was successfully able to synthesize cholesterol in the laboratory, achieving one of the first total syntheses of a steroid molecule.

    Original Title

    Sintesis Del Colestero

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    © Attribution Non-Commercial (BY-NC)

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    1) Woodward synthesized cholesterol through a 28 step total synthesis process involving the use of reagents like sodium hydroxide, hydrochloric acid, lithium aluminum hydride, acetic anhydride, and osmium tetroxide to transform intermediates into the final product. 2) The synthesis began with commercially available starting materials that were transformed through organic reactions such as acetylation, reduction, oxidation, and alkylation to slowly construct the cholesterol molecule. 3) After 28 steps involving over a dozen organic transformations, Woodward was successfully able to synthesize cholesterol in the laboratory, achieving one of the first total syntheses of a steroid molecule.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    118 views4 pages

    La Síntesis Total de Colesterol: R. B. Woodward

    Uploaded by

    Hector Martinez Gregorio
    1) Woodward synthesized cholesterol through a 28 step total synthesis process involving the use of reagents like sodium hydroxide, hydrochloric acid, lithium aluminum hydride, acetic anhydride, and osmium tetroxide to transform intermediates into the final product. 2) The synthesis began with commercially available starting materials that were transformed through organic reactions such as acetylation, reduction, oxidation, and alkylation to slowly construct the cholesterol molecule. 3) After 28 steps involving over a dozen organic transformations, Woodward was successfully able to synthesize cholesterol in the laboratory, achieving one of the first total syntheses of a steroid molecule.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 4

    La sntesis total de colesterol R. B.

    Woodward
    CH3 CH3 CH3 2 HO 3 H A 4 11 10 B 6 H 12 C 8 14 H 13 D 15 17 H 16 18 19 CH3 CH3

    1
    5

    9
    H 7

    colesterol

    O CH3
    +

    O CH3

    100 a
    CH3O

    C 14
    H

    1. NaOH 2. HCl b

    CH3O O

    O CH3 LiAlH4

    OH CH3 H2O - H+

    c
    CH3O H O OH CH3O H

    CH3

    1) Ac2O, piridina 2) Zn 3) H+

    CH3 EtONa/ HCO2Et

    e
    O H OH O H

    CH3 (CH3)3COCH2 = CHCOCH2CH3 O H H O

    CH3

    C
    O H CHO

    KOH

    g
    H

    7
    O

    CH3 OsO4

    CH3 OH CH3COCH3

    C
    CH3

    H H

    C
    CH3

    H H

    D
    OH

    B
    O

    B
    O

    10

    CH3 O H H3C O H O O

    CH3

    H2, Pd k
    H 3C 10

    11 9 H 8

    O H

    11

    12

    CH3 O
    1) CH3ONa / HCO2Et 2) PhNHCH3

    CH3

    H O H 1) -OH / N C

    O HC N

    m
    Ph

    CH3

    13

    CH3 O CH3 N C H O CH N H O C(CH3)2 CH3 10 CO2H O H

    CH3 O C(CH3)2 O H

    KOH, H2O n

    Ph CH3

    14

    15

    CH3 O CH3 NaOAc / Ac2O

    CH3

    C
    H

    D
    O H

    O C(CH3)2 1) CH3MgBr 2) KOH CH3 H O H O C(CH3)2

    A o
    O O

    16

    17

    CH3 HIO4 CH3

    CHO NH2+ -OAc

    CH3 CH3

    CHO

    C
    H CHO H

    C
    H

    D
    H

    A
    O

    B
    18

    A
    O

    B
    19

    CH3
    1) Na2Cr2O7 / HOAc 2) CH2N2 3) Resolver

    CO2 Me

    CH3 CH3 H
    5

    CO2 Me H

    CH3

    H H

    1. H2 , Pt 2. CrO3, HOAc t
    O

    H H

    s
    O

    20

    21

    O C Cl CH3
    1) NaBH4 2) KOH /H2O 3.piridina / Ac2O 4. SOCl2

    OH CH3 CH3 H HO H
    23

    CH3 H

    H H

    1) (CH3)2 Cd 2) BrMg - (CH2)3CH (CH3)2

    H H

    AcO

    H
    22

    CH3 CH3
    1. Ac2O / HOAc, 2. H2 , Pt 3. KOH , H2O

    CH3 CH3
    Na2Cr2O7 / H2SO4

    CH3
    3

    H H

    CH3 H O H
    25

    H H

    H
    4

    HO

    H
    24

    CH3 CH3
    Br2

    CH3 CH3
    NaI / 2,4, 6 trimetilpiridina

    Br

    CH3 H

    H H

    CH3 H

    H H

    O Br

    H
    26

    O
    27
    CH3 CH3 CH3 H

    CH3 CH3 CH3 H AcO H H

    CH3COCl aa

    1. OH 2. NaBH4 , CH3OH, H2O


    bb
    HO

    C
    H H

    28

    Colesterol

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