Chemistry of

Natural Products

Dr. Mohamed Rabie

 OH n Acylation OAc n
Alkaloid Alkaloid
 FeCl3
Phenolic OH Colored Product
Dehydration
Alcoholic OH Unsaturated compound
Oxidation
Alcoholic OH Aldehyde, Ketone, or Acid
 COOH aq. Na2CO3 Alkaloid
COONa
+ CO2
Alkaloid
 O
Alkaloid Oximes, Hydrazones

COX H3O+ COOH

Alkaloid Alkaloid
aq. Na2CO3
X = OR, NHR
COONa
Alkaloid + CO2
 OMe n HI
OH n + CH I
Alkaloid 126oC Alkaloid 3

AgNO3
AgI
Yellow ppt
vi) -OCH2O- group
CH2
O O OH OH
HCl
Alkaloid Alkaloid + CH2O
 Example:
Alkaloid R2NH
N
R R

2HI NH2 n + 2CH I AgNO3

NMe2 AgI
Alkaloid n Alkaloid 3
126oC Yellow ppt
 H H
H
H
 1) CH3I 
 
2) AgOH
N(CH3)2 N+(CH3)3 OH-

Heat H

-H2O
-NMe3
 H2 H2
C C
H2 / Ni H2C CH2 1) CH3I H2C CH2
H2C CH2 H2C CH2
N N 2) AgOH N
H OH -
Pyridine H3C CH3
Piperidine
N,N-Dimethylpiperidinium hydroxide

H2 H2
C C
Heat H2C CH 1) CH3I H2C CH Heat
H2C CH2 H2C CH2
-H2O 2) AgOH -H2O
N(CH3)2 -
N(CH3)3 OH

H2 H
C C
HC CH Isomerization HC CH
+ (CH3)3N
CH2 CH2 CH2 CH3

Piperyline
Emde Degradation: For Alkaloids with no -hydrogen
Na 1) CH3I
N NH
EtOH 2) AgOH
Isoquinoline

Heat CH3I
CH3
N OH - N(CH3)2
CH3 -H2O
Hoffmann

Na - Hg
+ (CH3)3N
I-
N(CH3)3 H2O - EtOH CH3
Emde 2-Methylstyrene
 CH3 AgOH
N Heat N(CH3)2
- CH3 Hofmann
I
1) CH3I
H2 - Pt 2) Na - Hg
Emde
Hofmann + (CH3)3N
N(CH3)2
CH3
2-Methyl styrene
 Na - Hg Hofmann
Emde
N I- N
H3 C CH3
H3 C CH3 + (CH3)3N

AgOH

Hofmann N
-H2O
Heat H3C CH3

N OH -
-MeOH
H3C CH3
N

CH3
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