H3C CH3
H3C CH3
1. BH3
2. NaOH, H202
t    H © 0:)-PPh3 H
„OH
H3C CH3
X
PCC
H3C CH3
7)
O
X
O CH3
CH,
O
x
Cľ"^CH3 AICI3
CH,
NaBHa
H20
O
x
C|-^CH3 pyridin
OH
CH,
8)
H,C
OH OH
O
H,C
CH,
NalO,
H3C
1. CH3MgBr
2. H+ (zprac.)
H3C
o
pH = 4-6 N' NaBH3CN
OH pec ACH3 '
O
H3C^^^CH3
10)
o
1. Hg(OAc)2, H20
2. NaBH4
OH
CH,
1. LDA, -78 °C
H CH3 3. H+ (zprac.)
PCC
^ H3C CH3
1. LDA, -78 °C
2. O
x
EtO OEt
O O
OEt
1. NaOEt
2. CH3I
H3C^r"(DEt CH3
Ho—OH H+ odebírání vody
O O
H3C    y OEt CH3
OH
12)
H
NyCH3 O
SOCI2 pyridin
Cl
NaCN
CN H*Pd/C
O pyridin Cľ CH3
NH2
OH
13)
PCC
O
1. Et2CuLi
2. H+ (zprac.)
H © e:>—PPh3 H
CH3
HO.
OCHo
MCPBA
o:
CH-,
CHo
CH3OH, H2S04
CH3
14) H3C-N-CH3
.CH3
H+, H20
OH
CH3
NO,
NaBH4 H20
HN03 CH3 H2S04
O
CH3
N02
15)
H2 Lindlar
CH — ch
Br NaCN CHo
CN
H+, H20 AT
CHo
CH2N2
16)
Br
- O)
HBr, R.
Br
Br
'N3    H2, Pd/C    r^^/\/NH2 LDA " ^Br
NH2
17)
(CH3)2CuLi
Cl
H,C
ČH,
"CH
3 H,0
H 0 G^PPhg H
CH3
O
H3C CH3 odebírání vody
HO   Y CH3 OH
HO   y v CH3 OH
18)
OzN NaOCH3
/VOCH3
COOCH3
H2, Pd/C
02N
OCH3 Br2
OCHa   co2       j^^0ch3 ch3br
FeBr3   OzN'^^Br 02N'        "MgBr 02N' ^ "COOw 02N' "v-í" "COOCH3
.O
OCH3
21) S
Br
>vOEt
(±)
MCPBA (1 ekv.)
Br2 EtOH
Ph.s,o
AT
o