natural products-cholesterol synthesis

3
Natural Products Prepared by: Mr:Mohammed H. Raidah 2008-2009

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Cholestrol synthesis with the mechanisms

TRANSCRIPT

Page 1: Natural Products-cholesterol Synthesis

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Natural Products

Prepared by:

Mr:Mohammed H. Raidah

2008-2009

Page 2: Natural Products-cholesterol Synthesis

O

O

MeO+ 100Co

HO

O

MeO

NaOHHCl

O

O

MeOH

LiAlH4

HOH

OH2

MeO

OH2

OHH

H2SO4

OH

O

ZnRed.

NaOMe

EtO2CH

C OOEt

H HC

HO

OH

KOBut

EVKH

O

Et CO

HO

O

KOH

HO

H

CH3C

H

H

OsO4

HO

H

OH

OHMeCOCuSO4H

O

H

O

OH

CO

Me

Me

HO

HO

CO

NHMePh

NaOMe,HCOOEt

CO

OEtH

HO

HO

CO

HC O

HO

HO

CO

H

NMePhHOH

H

O

HO

CO

CHNMePh

CN

OH HH

O

HO

COH2,Pd

COO

H

H

HO

CO

OOH

OH

H

HO

CO

OO

NaOAcMe MgBr

KOH

H

HO

CO

OO

HC

H

HO

CO

OHO

H

H

HO

CO

OHIO4 H

H

O

O

O

H

NH OAc

H

H

O

CHO

Na2CrO7

CH2N2

H

H

O

CO2Me

H2/Pt

CrO3,AcOH H

H

O

CO2Me

H

H

H

NaBH4,KOH

AC2O,SOCl2OC

O

CO Me

Me

Page 3: Natural Products-cholesterol Synthesis

With my best wishes

H

H

AcO

C

H

H

H

O

Me

C6H13MgBr

H

H

AcOH

H

H

OH

H2/Pt

Ac2O, AcOH

H

H

HOH

H

H

H

Na2Cr2O7

H

H

OH

H

H

H

Base

Br BrH

H

OH

H

H

Dehydrohalogenation

H

Ac2O

OC

O

CO Me

Me

H

H

AcOH

H

H

H

H

HOH

H

H

NaBH4, MeOH, H2O