Natural Products-cholesterol Synthesis
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Natural Products
Prepared by:
Mr:Mohammed H. Raidah 2008-2009
O
MeO
HCl
MeO
O
O Me O C Me
O H
OH
H
H
MeO O
OH MeCO CuSO4
OsO4
H
H
H O H
O C
O
NaOMe,HCOOEt NHMePh
O
HC O
OEt O
H
H
O HC
OH
H
H
O
O
H
O
O C
H
NMePh
C
H
O
CHNMePh
O
H
O
O H
O Me MgBr
O
H O
O
C NaOAc
O
O
CHO
H
HIO4
H O
O
NH OAc
H
H O
H
H O
OH
CO2Me
H H
H2/Pt
H O
O
H CO2Me
Na2CrO7 CH2N2
C
H
O
C H
CN
O
C
H
H
KOH
O O
H
O
OH
O
H H
EVK
O
H
C
H
O
H
O
O C
H
H
H
C
O Et C
O
H
O
O
C
H
O
H
H
O
C
H
HO
O
H C O OEt
KOBut
H3C H C H O
H
O
O
H
KOH
H
OH
O H2,Pd
EtO2CH O
OH
OH
O
C
H
H
NaOMe
OH2
O
H
O
MeO
H
Zn Red. O
H2SO4
LiAlH4
NaOH
100Co
+
OH2
O
O
H
CrO3,AcOH
O
O
O C Me C O Me
H
H
NaBH4,KOH AC2O,SOCl2
H
H
H
H
O
Na2Cr2O7 H
H HO
H
H
H2/Pt
H
Base
H
O
H AcO
H H
H
H
H
H
Ac2O
H
H
H
NaBH4, MeOH, H2O
AcO
H HO
H
O O C Me C O Me
With my best wishes
H
H
H H
Br Br
H AcO
H
C6H13MgBr
H
Ac2O, AcOH
H Dehydrohalogenation
O C Me H
H
H
H
H
OH
H
H
H
Prepared by:
Mr:Mohammed H. Raidah 2008-2009
O
MeO
HCl
MeO
O
O Me O C Me
O H
OH
H
H
MeO O
OH MeCO CuSO4
OsO4
H
H
H O H
O C
O
NaOMe,HCOOEt NHMePh
O
HC O
OEt O
H
H
O HC
OH
H
H
O
O
H
O
O C
H
NMePh
C
H
O
CHNMePh
O
H
O
O H
O Me MgBr
O
H O
O
C NaOAc
O
O
CHO
H
HIO4
H O
O
NH OAc
H
H O
H
H O
OH
CO2Me
H H
H2/Pt
H O
O
H CO2Me
Na2CrO7 CH2N2
C
H
O
C H
CN
O
C
H
H
KOH
O O
H
O
OH
O
H H
EVK
O
H
C
H
O
H
O
O C
H
H
H
C
O Et C
O
H
O
O
C
H
O
H
H
O
C
H
HO
O
H C O OEt
KOBut
H3C H C H O
H
O
O
H
KOH
H
OH
O H2,Pd
EtO2CH O
OH
OH
O
C
H
H
NaOMe
OH2
O
H
O
MeO
H
Zn Red. O
H2SO4
LiAlH4
NaOH
100Co
+
OH2
O
O
H
CrO3,AcOH
O
O
O C Me C O Me
H
H
NaBH4,KOH AC2O,SOCl2
H
H
H
H
O
Na2Cr2O7 H
H HO
H
H
H2/Pt
H
Base
H
O
H AcO
H H
H
H
H
H
Ac2O
H
H
H
NaBH4, MeOH, H2O
AcO
H HO
H
O O C Me C O Me
With my best wishes
H
H
H H
Br Br
H AcO
H
C6H13MgBr
H
Ac2O, AcOH
H Dehydrohalogenation
O C Me H
H
H
H
H
OH
H
H
H
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