TERM TEKNIK PENDEKATAN DISKONEKSI

(Christica Ilsanna Surbakti S.Farm. Apt.)

MOLEKUL TARGET : MOLEKUL YANG DISINTESIS.

ANALISIS RETROSINTETIK : ADALAH reaksi mundur melalui PROSES PEMBELAHAN

MOLEKUL TARGET KEDALAM MATERI START YANG
TERSEDIA DENGAN INTERKONFERSI GUGUS FUNGSI (IGF) DAN DISKONEKSI.

ITERKONFERSI GUGUS FUNGSI (IGF) : PROSES PENGUBAHAN

SUATU GUGUS FUNGSI KEDALAM GUGUS YANG LAIN
DENGAN : reaksi SUBSTITUSI , ELIMINASI, OKSIDASI DAN REDUKSI SERTA
OPERASI BALIK YANG DIGUNAKAN DALAM `` ANALISIS.

DISKONEKSI : OPERASI BALIK SUATU REAKSI PEMBELAHAN

YANG DIBAYANGKAN DARI SUATU IKATAN AGAR
“MEMUTUS” IKATAN MOLEKUL untuk nemperoleh sinton DENGAN SIMBUL

( SIMBOL UNTUK DISKONEKSI DAN IGF)

 SINTON : FRAGMEN IDEAL, BIASANYA SUATU KATION
ATAU ANION, YG TERJADI AKIBAT SUATU DISKONEKSI. MUNGKIN
ATAU MUNGKIN TIDAK MERUPAKAN “ZAT ANTARA”
DALAM REAKSI BERSANGKUTAN YG STARA DENGAN SUATU PEREAKSI.
REAGEN : SENYAWA YANG DIGUNAKAN DALAM PRAKTEK
UNTUK SINTON.

CONTOH :
CH3I MERUPAKAN REAGEN DARI SINTON CH3+.

O O O O-

H3C C Cl H3C C+ H3C C OC2H5 H2C C OC2H5

REAGEN SINTON kation

O O

H3C C CH3 H3C C+

O-
reagen sinton kation OH HO
HO
reagen sinton anion
REAGEN UNTUK SUBSTITUSI ELEKTROFILIK
AROMATIK

H X
X+
R R
 RANTAI SAMPING AROMATIK OLEH IGF
Y X

R R

Y X REAGEN

REDUKSI
-NO2 -NH2 H2, Pd, C, (Sn, HCl PKT)
-COR -CH(OH)R NaBH4
-COR -CH2R MIS; Zn/Hg, HCl PEKAT
OKSIDASI
-CH2Cl -CHO HEKSAMIN
-CH2R -CO2R KMnO4
-CH3
-COR -OCOR R’CO3H
SUBTITUSI
-CH3 -CCl3 Cl2, PCl5
-CC -CF3 SbF5
CN -CO2H HO- , H20
 HONO Z-
Ar-NH2 ArN2 ArZ

Z REAGEN

HO H 2O
RO ROH
CN Cu(I)CN
Cl Cu(i)Cl
Br Cu(I)Br
I KI
Ar ArH
H H3PO2 ATAU ETOH/H+
DISKONEKSI ETIL ASETOASETAT
A. O-
O O O
C +
3HC C OC2H5 C+ C OC2H5
3HC
H H H H
sinton kation sinton anion

O O
C
DIPILIH ?
C
3HC OC2H5 3HC OC2H5

SINTON I = SINTON II = ETIL ASETAT

B
O O O O-
+ C
C +C
3HC C OC2H5 OC2H5 3HC C
H H H H
sinton kation sinton anion

O O
C
C2H5O
C
OC2H5 3HC C H
H H
DIETIL KARBONAT ASETON
 MEKANISME REAKSI ETIL ASETO ASETAT

- O-OH
O O H2
H 3HC C C CH
CH3O- C C OC2H5
H2C OC2H5 H2C OC2H5 OC2H5
CH3OH
O
C -C2H5O-
3HC OC2H5

O O
C
3HC C OC2H5
H H
 1,3 di O

O O -
1,3 di O O
C C O
1. 3HC C CH3 C
H2 C+ H2C CH3
3HC
SINTON SINTON

O O O
C ATAU C
C
3HC Cl 3HC OC2H5 H3C CH3
ASIL KLORIDA ETIL ASETAT ASETON
RETRO SINTETIK PERFUMERY
-
O 
O O +
C  - O
C C CH2- +C
C CH3
H2 + CH3

sinton anion sinton kation

O
C O
CH2 C
H C2H5O CH3

ASETO PHENON ETIL ASETAT

 -
MEKANISME REAKSI O
- C
O  CH2
+
C  - O
CH2
C
H C2H5O CH3
-
C2H5O

O O O O-

C C C C
C CH3 - C CH3
H2 C2H5O H2 OC2H5
 RETROSINTETIK 1,3 DI OH
CH3
H2 CH3 IGF 2HC C
H3C C
C C H H3C C O
H3C OH OH REDUKSI H3C OH
 -HIDROKSIKETON
OH O-
C + + C
SINTON I DAN KE II SAMA H2C CH3
H3C CH3
SINTON I SINTON II

O
MOLEKUL / REAGEN ASETON
C
H3C CH3
REAKSI DAN MEKANISME REAKSI CH3
O O- 2HC C
Ba(OH)2
H3C C O
C C
H2C CH3
-H2O
H2C CH3 H3C O-
OH
H - ASETON O H
OH C -
- OH
H3C CH3
ASETON CH3
CH3 H2 / Ni 2HC C
2HC CH H3C C O
H3C C OH H3C OH
H3C OH
 -HIDROKSIKETON
 ANALISIS RETROSINTETIK BENZOKAIN

- CH3O -
OCH 3 SINTON
CH3OH
REAGEN = ETANOL
OH

+ C O - +
C O C O

NH 2
NH2
NH2
SINTON REAGEN = p-AMINO BENZOAT

IGF

OH

CH3
CH3 C O

IGF
C-N

NITRASI

NO2
NO2
TOLUEN p-NITRO TOLUEN p-NITRO BENZOAT
 MEKANISME REAKSI.
O + O -H-OH O CH3
H O N
H O N H +N
+
O O O
O
O
CH3
HO S OH
- O S OH CH3
O
OH NO2
O
OH
C O
C O +
REDUKSI
NO2 o-NITRO TOLUEN TAK
LARUT
pNITRO TOLUEN LALUT

NH2
REAGEN P-AMINO BENZOAT NO2
 ESTERIFIKASI ESTER

OH OH
+
H OCH3 H OCH3 OCH3
+
C O C OH
+ HO C OH H O C OH C O
H +
HOCH3 PERPIDAHAN
-H2O

PROTON
NH2
NH2 NH2
REAGEN P-AMINO BENZOAT NH2 NH2
 RETROSITETIK PARASETAMOL

O O
O
H3C C HN H3C C HN
H3C C HN
IGF IGF

HO O2 N
H 2N

O
H3C C HN

H2SO4 + HNO3 PEKAT +NO2

REAGEN -
SINTO ANION SINTON KATION
 O O O
H3C C Cl H3C CH +
O H3C C HN
SINTON
H 3C C ASIL KLORID ANION
O -
H 3C C HN
H2N
O REAGEN
ANHIDRI AS. ASETANILID
ASETAT
SINTON
REAGEN KATION
ANILIN

+NO2 H2SO4 + HNO3 PEKAT

O 2N
SINTO ANION REAGEN
-

REAGEN
BENZEN
SINTON KATION
 O
H3C C
O
H3C C
ATAU
O + O -H-OH O
H O N
+ NO2 O 2N O
H O N H
H 2N
O Zn + HCl
O O
O -H+ C Cl
HO S OH
- O
O
S OH
CH3
O
O
H3C C - HCl
- OH
O
O
O O H3 C C NH
H3C C HN
H3C C HN H3C C HN
Zn + HCl +NO2

- HCl
HNO2 + HCl
AZOTASI REDUKSI O2N
N N H2N

O TERJADI JUGA ORTO, UNTUK

H H MENGATASI MASALAH PENAMBAHAN
SUBTITUSI NUKLEOFILIK HNO3 DAN H2SO4 PEKAT HARUS
AROMATIK DIBAWAH 60 oc . LEBIH
O MENGUNTUNGKAN DARI YANG
PERTAMA. KARENA EFEK STERIK
H3C C HN
SEHINGGA SUBTITUSIELEKTROFILIK
KEARAH PARA LEBIH BANYAK

HO
 RETROSINTETIK PARASETAMOL

-
O O O

- C + C+ C
 CH3
HO N CH3 CH3 H
H
SINTON REAGEN ASETALDEHID

HO NH- HO NH2

IGF
SINTON REAGEN
p-HIDROKSI ANILIN

C-N
HO HO NO2
NITRASI
MEKANISME REAKSI SINTESIS PARASETAMOL

HO m-NITRO FENOL (LARUT)

HNO3 P
HO O2N
H2SO4 P

HO NO2
p-NITRO FENOL ( MENGENDAP)
H2
REDUKSI

HO NH2
O

C O
HO N CH3
H
3HC C

H3C C

O
 RETROSINTETIK FENIL PROPANOL AMIN
+  -
HC NO2
OH
- - H 2C NO2
IGF OH + - CH3
H + H   CH3 -
C C NH2 C C NO2
- SINTON REAGEN
H CH3 H CH3
+
-
O OH
+
C
C
H H

REAGEN SINTON KARBOKATION

MEKANISME REAKSI FENIL PROPANOLAMIN

O H - OH RED. H2 OH
+  H H
C + HC NO2 C C NO2 C C NH2
-
H  Zn + HCl
CH3 H CH3 H CH3
 RETROSINTETIK AMFETAMIN
H H + - IGF -
H IGF
 C C NO
+
C C NO2
C C NH2 2

H CH3 H CH3 H CH3

O
+
H2C NO2 HC NO2 + C C+
CH3 CH3 H H
REAGEN NITRO ETAN SINTON KARBOKATION REAGEN ASELDEHID SINTON KARBOANION

MEKANISME REAKSI AMFETAMIN

+ 75% H2SO4
O H  - OH 100% -
H C NO2 H
C + C C NH2 C C NO2
CH3
H H CH3 -H2O
H CH3

Pd / C DALAM ETANOL H2

H
H
C C NH2
H CH3
 RETROSINTETIK SALBUTAMOL

HOH2C
OH HOOC
HO C CH3 IGF
+ O
- CH3
C - CH3
H H2C N C CH3 HO
 + HN C CH3
IGF
H CH3 H2C N C CH3
H CH3
H CH3
- REAGEN
Br
C-N
HOOC
+ HOOC CH3
C-Br - O  +
Br2 C + + O N C CH3
HO
 + HO
C -
BROMIN CH2  H CH3
CH2
Br -
+ 
REAGEN SINTON KATION SINTON ANION
HOOC
-
O
+C
HO
- HOOC HOOC
CH3  O
+ O Cl
HO - HO + C - C -
REAGEN  
CH2 CH2

SINTON REAGEN SINTON REAGEN

 MEKANISME REAKSI SALBUTAMOL

HOOC
HOOC
O ASILASI -
Cl O
HO
+ C +C
CH2
HCl HO
-
CH2
Br -NaBr
H
Br
CH3ONa
HOOHC
O
HOOC
O HO C
LiAlH4 1 CH2
HO C CH3 S
H N
H2C N C CH3
REDUKSI -HBr Br
HOH2C CH3 H
H H3C
OH
HO C CH3 H3C C NH
H H2C N C CH3 H3C
H CH3
SALBUTAMOL
 RETROSINTETIK PROPIFENAZON
N NH2
+
O N - O
CH3 N

N N-C
O N

CH3
REDUKSI
+ +
N N

PROPI FENAZON +
O

CH3

CH3
O +
DIAZOTASI
O
OC2H5 O
NH2
-
CH3

O
O
OC2H5 3HC C OC2H5
 MEKANISME REAKSI PENAZON
O
O
O
KONDENSASI
CLAISEN 2HC C OC2H5
- 2HC C OC2H 5
2HC C OC2H5

-H2O O H3C C O-
H
C2H5O-
3HC C OC2H5 OC2H5 O
- C2H5ONa
2HC C OC2H5

NH2 H3C C O
+ NH2
N N ETIL ASETOASETAT
HN
HNO2 + HCl REDUKSI

AZOTASI
O

C2H5O C CH2

-O C CH3
O
O H N H
C2H5O C CH2 +
HN
CH3 C2H5O C CH2 PROTON S
HO C CH3
C CH3
H N
N
N HN
O N
HN

-C2H5OH
 RETROSINTETIK METAMPIRON
H
H + -
COSO CH2- H -CH2
H2 H3C N H3C N- H
-
H3 C N CH3 CH3 CH3
H3C N CH3 H3C N CH3
C-O N N
N CH3 CH3
N CH3 O N O N N
CH3 O N CH3
O N O N

N-C

SINTON REAGEN
REAGEN SINTON
O O +
IGF
- H2SO3
S O H C H HCH
OH SINTON REAGEN REAGEN SINTON

CH3+ CH3Cl
SINTON REAGEN

C-N C H
H3C N CH3
-
H
N C H
CH3 C H N
+ CH3
C N O N
CH3 -N
+ CH3
N
CH3
O N SINTON
N
O CH3 N
H N O CH3
+ N

C O

REAGEN
SINTON

- REAGEN SINTON -
H
 RETOSITETIK METAMPIRON LANJUTAN

-
-
H2 N - - CH3 H
CH3 CH3
-
O2N
CH3
N NO2+ N N
O CH3 CH3 CH3
N SINTON O N O N
N
CH3
O N
IGF HNO3 + H2SO4
REAGEN
REAGEN

SINTON REAGEN AMIDOPIRIN

H -
CH3+ H
CH3Cl - CH3
- - N CH3 N
NH2 N N HN + CH3 +
H2N
IGF + N +N SINTON +
O
-
CH3
H2C C

C O
ANILIN O
OC2H5
DIAZO
REAGEN ETIL
ASETOASETAT
 MEKANISME REAKSI METAMPIRON
+
O N OH - H2O
O N OH + H+ H

O N+
H
LAMBAT
N O N+ H H
-H+ CEPAT
H ELEKTROPILIK + N N O
N N O PROTONS REARR
NUKLEOPILIK
H

+
+ N N OH N N OH
N N N N+
- HOH H
- - CH3
H+
+ -

N CH3 H2C C
 +N -
O
3HC Cl C O H H2 H
Cl - H-H O
O C C CH3 O C C CH3
OC2H5
N CH3 C C
HN N CH3
N CH3
C2H5O C2H5O HN
HN

-HO-
MEKANISME REAKSI METAMPIRON LANJUTAN

O HN
- H+
C -
CH3 O2N
CH3
C2H5O
-
HO N O H
CH3
N
CH3 N
O N HCl+ Zn O
CH3
N N
CH3
O N
OH
-H2O
C H
HN CH3
CH3Cl
H
C H
N
O CH3
N
C H
H2O -H
O
HOH
N
CH3 H 3C N
C H CH3
- +N H
N
-Cl H3C CH3
CH3 N
O N CH3
O N
N
CH3
O
O N

- CH

O O
HO S H
S OH -O
O OH HO H
H H H C
H C CH + H C -H
H PENATAAN
-
H
-H
H3C N ULANG PROTON
H 3C N + CH 3
H3C N
+ CH3 H3 C N + CH3
CH3

N
CH3
N N O N
CH3 N CH3
O N O N
CH 3 H20 O N

METAMPIRON
 RETOSINTETIK DAN MEKANIME REAKSI ASAM MEFENAMAT
COOH COOH
COOH

+
Cl
SINTON REAGEN
NH

- NH NH2
CH3

CH3
CH3

CH3

CH3
CH3
SINTON REGEN

MEKANISME REAKSI ASAM MEFNAMAT

COOH
COOH
SUBTITUSI
NUKLEOFILIK + HCl
AROMATIK NH
Cl
H N H CH3

CH3

CH3

CH3
RETROSINTETIK ORFENADIN
H1 ANTAGONIS
CH3

H2 CH3 CH3 CH3

C -N
O N HN
C
C H2
CH3 CH3
SINTON CH3
H CH3 REAGEN
C-N
O CH2+
C
ORFENADIN C H2

CH3 H

SINTON
H2
O C
C Cl
C H2

REAGEN

CH3
H2 O
C CH3
+
H2C Cl
O S CH3
SIMTON + o
C
O
C+
H2 H
HO
C H
C Cl
H2
REAGEN
SINTON REAGEN
 O
CH3
CH3 -
O S CH3

O H O SINTON
C+
C
H O
H
HO S CH3

SINTON O
O REAGEN
O
IGF REDUKSI Cl
-HC C
CH3 O

HO S H2SO4
O

C O
SINTON SINTON +

CH3 CH3 CH3

- -
-

SINTON REAGEN SINTON

 SINTESIS ORFENADIN
H
CH3

CH3 H N H Na
SUBT. ELETR. O H
CH3 O, P
H
O C

C H
-
 + O -AlCl4
Cl
Cl 
C
Cl Al
Cl
-H2O
CH3
O

O H3C S OH
O
HO S OH O
C+
HO SH + H3C H
O
-H2O
H+
O
-

HO H2
C
C Cl
CH3 CH3 H2
CH3
H2 HN SUBT. NUKLP. O
O C
C Cl CH3
O S CH3
C H2
C
H O
H
CH3

H2 CH3
C
O N
C
C H2
CH3
H
RETRO SINETIK BENZHIDRIN ( N-[2-(DIFENIL METOKSI) ETIL] IROLIDINA
H1 ANATAGONIS
H2 C1 R=H
R1 C C2 R = 4-CH3
O N C3 R = 4-OCH3
C C4 R = 4-Cl
C H2
C5 R = 2,4 -DI Cl
H

C-N
R2 H2
- C H2
O N C
C HO N
H2 C
H2

R1 SINTON ANION REGEN

+
C
SINTON KATION
H

CH2
-
O N-
C
H2
R2
SINTON KATION + SINTON AION
O
R1
O S CH3

C
O H2
H C Cl
HO
C H N
H2

REGEN 2-KLO ETANOL REGEN PIROLIDIN

R2 O
O

-
O S CH3
HO S CH3
R1
O
O
C+
SINTON KATION SINTON TOLUEN SULFAT REAGEN TULUEN SULFAT
H

O O

HO S+ HO S OH
CH3 - CH3

O O
R2
REAGEN TOLUEN SINTON ANION SINTON REAGEN

R1 R1
O
OH R1 R1
C REAGEN C O O

H IGF C C
+
Cl
SINTON KARBOKATION BENZOIL KLORIT
-

R2 R2
DIFENIL METANOL BENZOFENON

SINTON KARBOKATION REAGEN

R2 R2
 MEKANISME REAKSI

Cl O

+ Al Cl HO S OH O
R1 H2O
O
Cl O HO S OH
C O
HSO4-
Cl O HO S
REAGEN
-AlCl4 R2 O

CH3
H
R1
R1 Na OH
O H B H
C REAGEN TOLUEN
C
H H
-NaBH2 O

HO S CH3

R2
H2
DIFENIL METANOL C Cl
HO
H2 C
H2
C
O Cl
C O
C H2
R1
H O O S CH3
-
C
HO S CH3 O
H

R2

H2
R1 C
O N
C
C H2

R2
BENZHIDRILETER
 RETROSINTETIK CAPTOPRIL

IGF
COOH N COOH
N O
H2 C H2
C - + CH C S C CH3
CH C SH  DISKONEKSI
O 
CH3 CH3
O
CAPTOPRIL C H2
 + CH C S C CH3 +
N- COOH
CH3
SINTON SINTON

Cl O
C H2
 CH C S C CH3
N COOH
CH3

REAGEN H
3-ACETHYLTHIO-2METHYL- REAGEN
PROPIONIC ACID CHLORIDE L- PROLIN
 MEKANISME REAKSI CAPTOPRIL

 N- COOH
N COOH
-
-CH3OH 
REAGEN Cl
H + O
L- PROLIN Na+ +
C H2
 CH C S C CH3
CH3ONa / NaOH
BASA KUAT MANA REAGEN
LEBIH MENGUNTUNGKAN CH3 3-ACETHYLTHIO-2METHYL-
PROPIONIC ACID CHLORIDE

O N COOH
O
C H2
H2N C CH3 - + CH C S C CH3


ASETAMID
CH3 H N H
+
H
N COOH

C H2
CH C SH
O
CH3 CAPTOPRIL
 ENALAPRIL PENGHAMBAT ACE

DISKONEKSI

H2C H2C
H2C CH3 CH2 CH2
CH2
(S) +
+ - CH N CH C
CH  C2H5O C C2H5O C
C2H5O C (S) N C (S) O
H
COOH O O
O O
SINTON ANION ETHYL 4-PHENYL
ENALAPRIL -2-KETOBUTYRATE
+
CH3

(S)
- CH N

HN HN C (S)
- HN
(S) COOH
(S)
O
COOH
COOH SINTON KATION
L-PROLIN SINTON KATION

CH3
CH3
-
CH3
CH (S) N
(S) CH (S) 
+ C
CH (S)
H 2N
H 2N C OH H2N + C _ COOH

_ O
O O DIPEPTIDE L-ALANIL -L-PROLIN
L-ALANIN
SINTON ANION
 IGF N PROTEKSI IGF
L- ALANIN
DERIVAT
t- BUTOKSICARBONIL CPROTEKSI
CH3 L- PROLIN ESTER
CH3
CH (S)
H3C CH (S) 
CH3
HN C OH H2
CH H2N C C
C O
H2C O O O

MEKANISME REAKSI
CH3

CH (S)
H3C CH3
HN C OH N H2
(S) C C
CH
H
C O
H2 C O O + O

N PROTEKSI CPROTEKSI
L- ALANIN + L- PROLIN ESTER
DERIVAT
t- BUTOKSICARBONIL

N C N

DCC = DISIKLOHEKSIL
KARBODIMIDA
 DCC = DISIKLOHEKSIL
KARBODIMIDA

CH2Cl OH
-
N C N

H
CH3

CH (S) N
H 3C CH3
(S) -
HN C H2
CH
C C
C O
H2C O
O
O
O

3FC C

OH

CH3

CH (S) N
H3C CH3
(S) -
HN C H2
CH
C C
+ C O
H2C O
O
O
H
- (CH3)2CHCH2OH
 CH3

CH (S) N
(S) -
HN C H2
C C
H
C O
+ CH3
O
O O
H
CH (S) N
H (S) -
N C H2
- CO2 + C C
H
C O
CH3 -H+ HO O
O

CH (S) N
H (S) -
N C H2 CH3
C C
H
O CH (S) N
H
NaOH O HBr N C
(S)
-NaBR
C
H OH
O
H2 O + O
C
C
CH2 DIPEPTIDE L-ALANYL-LPROLIN
ETHYL 4-PHENYL C O
-2-KETOBUTYRATE
C2H5O
 -H2O

H2C CH3 H2C CH3

CH2 CH2
(S) H
C CH
N N
CH CH
C2H5O C N C C2H5O C (S) N C (S)
H H
COOH OH COOH
O O
Na(BH3)CN /
H2/ Pd-C

H2 C CH3
CH2
CH
N
CH
C2H5O C N C
H
COOH
O O
ENALAPRIL
 OH
OCH3
H3CH2C

C C H3CH2C

CH2CH3 C C
IGF
CH2CH3

HO
H3CO
-
C2H5 C2H5 Mg Br IGF

SINTON KATION REAGEN

OCH3
OCH3
+

RETROSINTETIIK H3CH2C
OH H3CH2C
OH

DIETHYL STILBESTROL CH C+
C C

CH2CH3
H
SINTON ANION

H3CO
H3CO

OCH3

OCH3
O OCH3
H3CH2C
O
CH C O
H2
H+ C C
C C

H3CO

H3CO
H3CO
DESOXYANISON
SINTON ANION

+
C2H5+(SINTON ANION) C2H5I( REAGEN)
 MEKNISME REAKSI STILBESRTROL
H2
-
 OCH3
3HC C I OCH3
+ -
H O O
C2H5ONa H3CH2C
+
C C CH C
-
 + - -
 + 
H C2H5 Mg Br
-NaI
- C2H5OH
H O
H3CO H
H3CO O H
DESOXYANISON MgBr OCH3

H
O
H3CH2C
OCH3
CH C
+
H OH
H3CH2C
-
-HBr C2H5
C C

CH2CH3
-Mg(OH)2
H
H3CO

H3CO
- H+ DEHIDRASI
OH

OCH3
H3CH2C

+ 2HBr C C
H3CH2C -2CH3Br
CH2CH3
C C IGF
CH2CH3

DIETHYL STILBESTROL
HO

H3CO
 RETROSINTETIK KROMOGILAT

O O
-
HO C C OH O O

+
O O O O C2H5O C - C OC2H5

+ -
H2 H H2
 
R IGF
O O O O
R O C C C O
OH H2 H H2
R O C C C O R
OH

- - - O
o o O o-

H2 H H2 C2H5O C
R O C C C O R
OH
SINON SINTON
 H 3C H3 C
- CH3
O
HO O HO O O OH
-
 H2 H H2 C2H5O C
R O R O C C C O R O
+ OH
SINTON OC2H5

H 3C - ETIL OKSALAT
H
+2HC C CH2 + REGEN
HO O
OH
R OH
SINTON

REAGEN

- -
H H
Cl2HC C CH2Cl 2HC C CH2Cl

O
OH
2',2' DIKLOR PROPANOL EPIKLORHIDRIN
YANG DIPILIH
 MEKANISME REAKSI KROMOGLIKAT

H3C CH3
H3C C2H5ONa
- CH3
HO O O C OH
HO O O OH
-
H +
R OH + 2HC C CH2Cl H2 H H2
HO R
R O C C C O R
O
OH
TURUNAN
DIHIDROKSI KONDENSASI
ASEOFENON EPI KLOROHIDRIN
-C2H5OH
-
ETIL OKSALAT ETIL OKSALAT
O O
OH O O
HO O O
C2 H 5 O C C OC2H5
C C
CH CH
- -C2H5OH -
HO O O OH C2H5O H2 C OC2H5 C2H5O CH2- OC2H5

H2 H H2 HO O O OH
R O C C C O R
H2 H H2
OH
R O C C C O R
OH
 O -H2O O

C2H5O C - C OC2H5

O O O O
-C2H5ONa
NaOH
H2 H H2 SAPPONIFIKASI
R O C C C O R
OH O O

HO C - C OH
ESRTER KROMON
O O O O

H2 H H2
R O C C C O R
OH

KROMOGILAT
 DISKONEKSI KROMONAR

CH3 CH3

C2H5 C2 H 5
H2 H2
H2 H2
N C C N
C C
IGF C2H5
C2H5
H2
HO O O
C2H5O C C O O O

KROMONAR
CH3
CH3
C2H5
C 2 H5 H2 H2
H2 H2 C C N
C C N
C2H5
C2H5 + O
HO O-
HO OH O
OC2H5
SINTON
 SINTON

O
O O

3HC C+ C C O C2 H 5 H
- 3HC C C C O C2H5
H2
H2 C C N C2 H 5 H2
H2C C N C2H5
HO OH C2H5
C2 H5
SINTON
SINTON REAGEN

O O
H2
+ H-
H2 C C N C2H5 3HC C C C O C2H5

HO OH C2H5
SINTON SINTON

O O
H2 H2
Br C C N C2H5 H2
3HC C C C O C2 H
5
C2H5
REAGEN
REAGEN ETIL ASETO ASETAT
2-KLOROETIL AMIN
 MEKANISME REAKSI KROMONAR

ETIL ASETOASETAT

O - O H2S4 /H+ O O

H H
3HC C C C O C2 H5 3HC C C C O C2 H 5
+ -
H2
H H2 H2 C C N C2 H 5
+ H2
Cl C C N C 2H 5
- +C 2H5 C2 H 5
2-KLOROETILAMIN
HO
OH FRIEDEL DAN
C2 H 5 C2H 5 CRAFTS
RESORSINOL KONDENSASI
O N C2 H 5 OH O

H
O C H2 C 3HC C C C O C2 H5
HO H2
3HC C C CH2
-H2O H2 C C N C2 H5
HO
C2 H5
ESTER CUMARIN
TAK JENUH

OH

OH
 CH3 CH3

C2H5 C2H5
H2 H2 H2 H2
C C N C C N

-C2H5OH C2 H5
C2 H5
HO O+ O C 2 H5 HO O O
-
O O
H
H2
Br C C OC2H5 -HBr
-
 +

CH3

C2 H 5
H2 H2
C C N

C2H5
H2
C2H5O C C O O O

KROMONAR
 CH3 CH3 H3C
H
H
HIGF H
IGF
O
OH +
HO -O
O HO O  O
HO O O -
HIMEKROMON

3HC
H
C
O +
C
H
+
HO -O
C
O

SINTON I SINTON II

3HC
H
C
O
C
H
C HO - OH
C2H5O O

SENYAWA SINTON I SENYAWA SINTON II

(REAGEN) = ETIL ASETO ASETAT (REAGEN ) = RESORSINOL)
 REKSOHADIPRODJO 1990

CH3
H 3C

C H
O C+ H
HO
H+ C
C
H
H
C
C
C O HO
OH C O
C2H5O
C2H5O
O
O
KONDENSASI
FRIRDEL- CRAFS -H+
CH3
CH3
H
-H2O
+ H
H OH2
-H+
O
O HO OC2H5
OH
HO OC2H5
OH

SUBTITUSI NUKLEOPILIK ESTER

CH3
CH3

O-
O-

O +
O OC2H5
H+ OC2H5

CH3

O
O
HIMEKROMON
 SUBITUSI NKLEFILIK
KARBONIL ESTER
3HC 3HC H3C
H H
C C H
O O
C C H
H H O
C H+ OC2H5
C C
WODD 1992 C2H5O O C2H5O OH +
HO O +
OH

HO OH PERPINDAHAN
PROTON

CH3 H 3C
H+ H
H
O
H
H
H -H+ O
C
C - C2H5OH HO OH
O O
HO O
+
O C2H5

H
KONDENSASI FRIEDEL-CRAFF
CH3
CH3
H H+
HO C+ H
-H+ HO
H
H H

C
O O C
HO O
HO O

CH3 CH3
H
+
H2O
H
-H+

HO -H2O C
O O O
O HO
 RETROSINTETIK KROMOGILAT

O O
-
HO C C OH O O

+
O O O O C2H5O C - C OC2H5

+ -
H2 H H2
 
R IGF
O O O O
R O C C C O
OH H2 H H2
R O C C C O R
OH

- - - O
o o O o-

H2 H H2 C2H5O C
R O C C C O R
OH
SINON SINTON
 H3C H3 C
- CH3
O
HO O HO O O OH
-
 H2 H H 2 C2H5O C
R O R O C C C O R O
 + OH
SINTON OC2H5

H3C - ETIL OKSALAT

H
+2HC C CH2+ REGEN
HO O
OH
R OH
SINTON

REAGEN

- -
H H
Cl2HC C CH2Cl 2HC C CH2Cl

O
OH
2',2' DIKLOR PROPANOL EPIKLORHIDRIN
YANG DIPILIH
 MEKANISME REAKSI KROMOGLIKAT

H3 C CH3
H3C C2H5ONa
- CH3
HO O O C OH
HO O O OH
-
H +
R OH + 2HC C CH2Cl H2 H H2
HO R
R O C C C O R
O
OH
TURUNAN
DIHIDROKSI KONDENSASI
ASEOFENON EPI KLOROHIDRIN
-C2H5OH
-
ETIL OKSALAT ETIL OKSALAT
O O
OH O O
HO O O
C2 H 5 O C C OC2H5
C C
CH CH
- -C2H5OH -
HO O O OH C2H5O H2 C OC2H5 C2H5O CH2- OC2H5

H2 H H2 HO O O OH
R O C C C O R
H2 H H2
OH
R O C C C O R
OH
 O -H2O O

C2 H 5 O C - C OC2H5

O O O O
-C2H5ONa
NaOH
H2 H H2 SAPPONIFIKASI
R O C C C O R
OH O O

HO C - C OH
ESRTER KROMON
O O O O

H2 H H2
R O C C C O R
OH

KROMOGILAT
 DISKONEKSI KROMONAR

CH3 CH3

C2H5 C2H5
H2 H2
H2 H2
N C C N
C C
IGF C 2H 5
C2H5
H2
HO O O
C2H5O C C O O O

KROMONAR
CH3
CH3
C2H5
C2H5 H2 H2
H2 H2 C C N
C C N
C2H5
C2H5 + O
HO O-
HO OH O
OC2H5
SINTON
 SINTON

O
O O

3HC C+ C C O C2H5 H
- 3HC C C C O C2 H5
H2
H2 C C N C2H5 H2
H2 C C N C2 H5
HO OH C 2H 5
C 2H 5
SINTON
SINTON REAGEN

O O
H2 -
+ H
H 2C C N C2 H5 3HC C C C O C 2H 5

HO OH C 2H 5
SINTON SINTON

O O
H2 H2
Br C C N C2 H5 H2
3HC C C C O C2H
5
C2 H 5
REAGEN
REAGEN ETIL ASETO ASETAT
2-KLOROETIL AMIN
 MEKANISME REAKSI KROMONAR

ETIL ASETOASETAT

O - O H2S4 /H+ O O

H H
3HC C C C O C2 H5 3HC C C C O C2 H5
+ -
H2
H H2 H 2C C N C2 H5
+ H2
ClC C N C2 H 5
- + C2 H5 C2 H 5
2-KLOROETILAMIN
HO
OH FRIEDEL DAN
C 2 H5 C2 H5 CRAFTS
RESORSINOL KONDENSASI
O N C2 H5 OH O

H
O C H 2C 3HC C C C O C2 H5
HO H2
3HC C C CH2
-H2O H2C C N C2 H5
HO
C2 H5
ESTER CUMARIN
TAK JENUH

OH

OH
 CH3 CH3

C2 H5 C 2 H5
H2 H2 H2 H2
C C N C C N

-C2H5OH C2 H 5
C2 H5
HO O+ O C2H5 HO O O
-
O O
H
H2
Br C C OC2H5 -HBr
-
 +

CH3

C 2H 5
H2 H2
C C N

C2H5
H2
C2H5O C C O O O

KROMONAR
 RETRO KLORAMFENIKOL
OH OH
H
H2C (R) O
+
O OCH3
C C
C
(S)
H
- + C C
O NH O-
 - Cl Cl Cl Cl
C N+
H H
SINTON
C O REAGEN
Cl Cl
H chloramphenicol +
OH OH
H
OH OH H2C (R)
C
H (S)
H2C (R) H
-
C NH O-
(S) -
H N+
NH O-
- O
N+
O C

O
CH3 IGF
 IGF
-
-
OH O
O
H + -
H 2C
  OH
-C C
 (S)
CH2 H H
NH O- +
- SINTON REAGEN
N+
O C -
+
CH3
O -
O
H
- 
+
O
H + --C
 
CH NH O-
- -
N+
 - O C
+ NH O
-  - +
N O
O C CH3
REAGEN
O
SINTON
CH3
-
O
-
H +

CH
+ - SINTON
- 
O C (CH3CO)O 
NH- O-
-
N+
CH3
REAGEN
SINTON O
 O
- - -
- O
H + IGF
 H +

CH
- CH
-
Br O -

NH2 Hcl O-
N + -
N+
REAGEN
O REAGEN
O

IGF
-
O
H +

CH
-
H O-
N+
REAGEN
O
 MEKANISME REAKSI KLORAMFENIKOL
O
HEXAMETHYLENTETRAMIN H3C C
ASAM ASETAN ANHID
O RUBERLEBIH
NH2 CH3COONa
H3C C
- N
 O
-
O H2N NH2 O
Br H + H+ O +
 ClH.H2N 
-HBr +
Br -CH Br  SN1
 - -CH
 -
- CH
H O - O  - H O-
N+ H O- HBr N+
3HC C N+
O OH O
ASET GLASIAL O H2N
p-NITROASETOFENON p- NITROFENIL BROMID- N +
p=NITROFENACILAMID HXCl

DELEPINE REAKSI H2N

KONDESASI ASETAMID
-H+
H
CH3
 H -H+
KONDESASI ASETAMID
CH3
H+ CH3
O
O C O
H OH O C
NH2
HO
HN (R) (R)
- +
N HN
 
C
-C H2N Br H
H C
H2 H
- O C -
H O
N+
H O-
H +
N
O
CH3 H ACETAMID O
H+
O
O C CH3
OH
H CH3
Al
HO
HN (R) (S) O CH
3
CH3 O C
C Al-ISOPROKSID O
C -
H2 H
-CH3COOH H O-
HN (R)
HO
+
N C
C -
REDUKSI SECARA H2
O MERWEIN-PANNDORF-VERLEY H O-
+
N

R,S-THREO-1-( p- NITRO FENIL)-2-ASETAMIDO-1,3-PROPANEDIOL

2 ATOM CHIRAL- O

ETOMELOL DERIVAT
MEMPUNYAI SATOM C CHIRAL
 -CH3COOH

CHCl2 CHCl2

C
O O C
OH
OH
OH
HN (R) (S)
HO
H2N (R) (S) HO
C
C C -
H2 H
C -
H2 H H O-
H -
O N+
+ CHCl2
N
CHCl2
O
C O C
O O OH
OH
(R)
OH HO
HN (R)
HO
H2N (R) (R)
C
C C - H
C H2
H2
- H
H O-
H -
O +
N
+
N
O
O

TERJASDI ENANTIOMER FRAKS INAS I DAN REKRES TAKIS AI

GENGAN (+)-CAMP HOR S ULFONAT
DALAM IS OP ROP IL ALKOHOL DAN
P ILIH YANNG D-(-)-THREO- CHLORAMFENIKOL
RETROSINTESIS IBUPROFEN
H3C CH3
IGF H3C CH3
H2
CH C C COOH H2
H CH C C COOC2H5
H3C H
H3C

IGF

H3C COOC2H5
H3C COOC2H5
H2
CH C C- +CH3 H2
CH C C CH3
H3C SINTON ANION
COOC2H5 H3C
SINTON KATION COOC2H5

CH3I REAGEN

H3C COOC2H5
H3C COOC2H5
H2
H2
CH C CH CH +
C CH-
+
H3C
COOC2H5 H3C
REAGEN COOC2H5
SINTON ANION KARBO KATION
H3C H3C
IGF COOC2H5
H2 H2
CH C NO2 CH C N NH
+ CH2
H3C H 3C

COOC2H5

REAGEN REAGEN
H3C
H2
CH C - + +NO2 H2SO4 PEKAT + HNO3 PEKAT

H3C REAGEN

SINTON KATION KARBO ANION

H3C
H2
CH C REGEN
H3C
MEKANISME REAKSI IBUPORFEN
O -H-OH O
O +
H O
H N +N
H O N

O O
O O
O
HO S OH
- O S OH

o CH3
O
H2C CH
H 3C
H2 CH3
CH C NO2
H 3C

Zn+ HCl
 +
O N OH + H+ O N OH
H - H2O
O N+
H3C H H
2 LAMBAT
CH C N O N+ H3C H
H2
H3C +
H ELEKTROPILIK CH C N N O
NUKLEOPILIK H3C
H

-H+
CEPAT
H3C PROTONS REARR
H2 H
CH C N N OH H3C H
2
H CH C N N O
H+ H3C
H3C H + H3C H2
2
CH C N N OH CH C N N+
H
H3C - HOH H3C
-
-

H3 C COOC2H5 H3C H
H2 2 +
CH C CH CH C N N
COOC2H5
H3C
COOC2H5 H3C
CH2

CH3I COOC2H5
-HI
 CH3I
-HI

H3 C COOC2H5
H3C COOC2H5
H3O+
H2
H2
CH C C CH3 CH C C
H
CH3
H3C -CO2 H3C
COOC2H5
-C2H5OH
+ H+
+ H2O
-C2H5OH

H3 C COOH

H2
CH C C
H
CH3
H3C
RETROSINTESIS KETOPROFEN
CH3
IGF CH3

C COOH
H C COOC2H5
H

C C

O IGF
COOC2H5 O

C- COOC2H5

C COOC2H5
+CH3
C CH3
SINTON ANION
O COOC2H5
SINTON KATION
C

O
CH3I REAGEN
 COOC2H5
COOC2H5
+
CH
+ CH-

COOC2H5
C COOC2H5
C O
REAGEN
SINTON ANION KARBO KATION
O

NO2 IGF COOC2H5

N NH
C
+ CH2
C
O
COOC2H5
O
REAGEN REAGEN
-

+ +NO2 H2SO4 PEKAT + HNO3 PEKAT

C
REAGEN
O

SINTON KATION KARBO ANION

C REGEN ( BENZOFENON)
 MEKANISME REAKSI.

MEKANISME REAKSI.
O H O
-H-OH O
C
H O N
H O+ N O
O
O O O
+N
- O S OH
HO S OH O

O O

C
KE META
NO2

Zn+ HCl
+
O N OH + H+ O N OH
H - H2O
O
C O N+
H
LAMBAT
N O N+
H ELEKTROPILIK
NUKLEOPILIK
 H
+
N N O
H
C
CEPAT -H+
PROTONS REARR O
H
N N OH
N N O
C H+
O C
O

+
N N OH N N+
H
- HOH
C -
C -

O O
 COOC2H5

CH +
N N
COOC2H5 COOC2H 5
C
C CH2
O CH3I O COOC2H5
-HI COOC 2H5

COOC2 H5
H3O+
C
H
CH3
C CH3
-CO2 C
COOC2 H5
-C2H5OH
C O
+ H+
O + H2O
COOH -C2H5OH

C
H
CH3

C KETOPROFEN
O
 RETROSINTESIS DIKLOFENAK
O

H2 O
C C
O
OH O
N
N IGF
NH IGF
Cl Cl
Cl Cl
Cl Cl

-
O
+
-
Cl O
Cl Cl O
+ - N
C O C O
O
- Cl Cl
C+ O N
C
SINTON Cl Cl
Cl REAGEN

REAGEN SINTON

N-
NH
Cl Cl
Cl Cl
SINTON REAGEN
MEKANISME REAKSI DIKLOFENAK
Cl O Cl
Cl Cl
C O O
- Cl Al Cl
C O
C O -
NH+
NH Cl -HCl Cl
O
Cl Cl - N
Cl Cl
Cl Cl
H
+
O
REAGEN
OH H -
CH + -
H2 - O
O
C N
H2 N
O
Cl Cl
N HOH Cl Cl
-H2O
Cl Cl

DALAM BASA

H2 O
C C
OH
DIKLOOFENAK
NH

Cl Cl
 R R

+
-
H CN
CH3 IGF CH3
-
C C
(S) CH2CH2 N (R) CH2CH2 N

CH3 + CH3
N
N

R Cl = CTM
C-C
Br
R

+
N CN
N CH3
+
DISKONEKSI
C
_
CH2CH2 N

SINTON CH3
CTM REAGEN SINTON

CN
CH3
Cl CH3 CH3 C
CH2CH2 N

CH2CH2 N + CHCH2 N H CH3

REAGEN
CH3 CH3
SINTON
REAGEN
R R

CN CN

C_ CH

H H
SINTON REAGEN

H
CH3
C
(R) CH2CH2 N

CH3
N

R = Cl = DEKSKLORFRNIRAMIN
 MEKANISME REAKSI SINTESIS CTM
R
R
Cl CH3
- CH3OH CN
CN CH2CH2 N
CH3
AlCl3 S
CH3 C
C -AlCl4+ CH2CH2 N
H H
SN1/SN2 CH3
H Br
CH3O-
-HBr
N

H
R
R H+
O H
C N
+
C NH CH3
CH3 (R)
C
(R) CH2CH2 N
C
CH2CH2 N
CH3
CH3
N
N

- H+
 -H+
R HO
O
R
OH H
C NH2
C NH CH3
CH3 C
(R)
(R) CH2CH2 N
C
CH2CH2 N
CH3
CH3 N
N

-NH3

R R
O

O
H C
CH3 H CH3
(R)
C
(S) C
CH2CH2 N CH2CH2 N

CH3 CH3

N
-CO2 N
DISKONEKSI KURKUMIN
H3CO OCH3
O O
H2
HO C C C C C C C OH
H H H H

IGF

H3CO OCH3
-O O-

H  + H2 H2 H2 +H
HO C C C C C C C OH
- +  + -
OH OH

H3CO

-O O-
2 +
HO CH
H2
-H C C C CH2-
2 C
- +  + - OH

SINTON ANION SINTON KATION

H3CO
O O
H2 2
H3C C C C CH3 HO C H

ETIL ASETO ASETAT M-METOKSI-O-HIDROKSI

BENZALDEHIDA (VANILIN)
 -
O - O -
-O
H -
CH3O- O 
H H

H
H2 H2
-
HC C C C CH- C- C C C CH-
M - +
H3CO
+ - - CH3OH - + + -

O -
E C H
HO
K +
CH3O-
N H3CO
H3CO
-
O H
HO
I H + H2
C C C CH2
HO
H  + H2
C C
-
C
+
CH2
-
HO
S OH
- + -
-CH3OH OCH3
OH

M
E HC OH

H3CO OCH3
R -O O-

H + H2 H2 +H
E
H2
HO C C C C C C C OH
- +  + -

A OH OH

K
-2H2O2

S H3CO OCH3

I
O O
H2
HO C C C C C C C OH
H H H H

KURKUMIN
 SINTESIS 4(FENIL– KURKUMIN DERIVAT)
O
-O O -O
 - H3C C
H H3C C
H3C C C C CH3
+ O
+ SINTON ANION
H3C C
O
-
O
O
-
HC - C CH3 REAGEN
R  + H3C C Cl
O -
3-FENIL-2,4-PENTADIENON
H2C - C CH3
 +

OH SINTON KATION
O OH
C R
O
CH C CH3
REAGEN
HC C CH3 IGF

IGF

R R

O
O
OH
H3C C
H3C C+
C O
O
SINTON ANION
CH- H3C C
+
REAGEN O
O

R H3C C Cl
 SINTESIS
OH
OH
CH3O-
O O O
C H
O H C
O C CH3 C C CH3
CH
+ CH- O
+ O CH
+
CH3OH C CH3

O
R
R
OH R
OH
OCH3
OCH3
-CO2
CH3O-
O H O

H 3C C HC C CH3
C O O O
C
-CH3OH
-
H -O O  H H 3C C
H H
H CH3COO- O
H2 C - C+ C - C+ CH
-2
     R

-FENIL ASETON DERIVAT

3-FENIL-2,4-PENTADIENON

B2O3 TRIBUTYL BORAT

BUTIL AMIN
 B2O3 TRIBUTYL BORAT
BUTIL AMIN

H3CO OCH3
-O O-
+
H  + H2 H H2 H
HO C C C C C C C OH
- +  + -
OH OH

R
-H2O
H3CO OCH3
O O

H
HO C C C C C C C OH
H H H H

4-(FENYL)-KURKUMIN DERIVAT

R
 DESKONEKSI CLOPINDOGREL
+
+
H2N
HN
- O
OCH3 S
Cl +C SINTON ANION
S

(S)
- REAGEN
HC +
N
-
O
OCH3 O
S +
Cl C OCH3
- Cl C
CH-
+
C
H Br
-


KENAPA ?
SINTON KATION
REAGEN

- O -
O
+
CH3+ CH3OH CH3
Cl +C O
SINTON REAGEN
OCH3
CH2 Cl C
Br-
SINTON
CH+

+
Br2
- O REAGEN
 - O-CLOR-METIL BENZIL ASETAT REAGEN
-
O
Cl +C - O - SINTON
OH
CH2 Cl +C

CH2

SINTON

REAGEN
O- CLOR-BENZIL ASETAT
 MEKANISME REAKSI
- O -
- O -
+C
OH
O
+
Cl CH3 O
Cl +C
OCH3
H+
CH2 - Cl C
 CH
CH3OH H CH-

+
CH3O- Br Br
REAGEN
O- CLOR-BENZIL AS ETAT
Br-

O
O
OCH3
OCH3
Cl C
Cl C
(S)
(R) C
C
H
+ Br H
H
Br
H
N

S N1 REAKS I
-HBr
S
S

-HBr S N1 REAKS I
O O
OCH3 OCH3
Cl C Cl C

(S)
N
HC (R)
C
N +
S
H

TERJ ADI RAS EMIS AS I

 DESKONEKSI SCOPOLITIN -OH
H
O H
O +
IGF
H3C
H3C
H H
C
C
-
O O O
HO O + O -
-
SCOPOLETIN

-OH
O O
H
H + -
H3C
H +
H H
H HO
HC O-
C + O -
O SINTON
C2H5O
SINTON
REAGEN ( ETIL MALONAT

H3C

H HO
OH
REAGEN
O C+ 1,3-DIHIROKSI
+ H METOKSIBENZEN
C+ C
H
O
C2H5O

SINTON SINTON

O
H C H

C
H OC2H5 C
O
C2H5O
REAGEN ETIL ASETAT
 REAGEN H
1,3-DIHIROKSI
METOKSIBENZEN O
-
O H3C - H
O OC2H5
REAGEN ETIL FORMIAT
C
+  - +
H OC2H5 HO C
H NaOC2H5
- -OHH
- H C H C H
H C H -Na+
+
+ C  C
C 
-C2H5OH -
- O- C2H5O
O
O C2H5O  -
C2H5O  -
H+
KONDENSASIFREIDEL-CRAFS
REAGEN ETIL ASETAT

MEKANISME O
H
H
H

SCOPOLETIN O C
C H
H3C
O C+

C
OC2H5
H
C
H3C C2H5O H -H+ HO C
H
C HO
OH
-C2H5OH C
HO O
OH O C2H5O

+ Na NaOC2H5
H+
H O
H O
H
H
O C
O C
H3C H
H3C H -H

C+
HO O O
HO O OH

H O+ H
H+
H
O C
O H H
H3C
H3C

C
-H2O
HO O O
-
O O O
SCOPOLETIN