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Lecture 1
OH
OH CHO
1. HCHO
A B C
MeO2C OH
2.
MeO2C OH
H O H O
HO O
3. NCOPh NCOPh
HO O
H O H O
D E
OH
4. Ph
Ph
OH
OH OH
5. O HO
O OH O G OH
F
TsHN O
6.
Ph OCH3
OH
NHTs
OH
7.
Lecture 2
OH
N CO2H
1. 1. 2. 3. 4. CO2Me 5.
OH N CO2H N
OH O
O
OH
6.
4. MnO2, benzene/reflux
Lecture 3
O
O OH
O CO2H
1. 1. CH3 CO2H 5.
Me 2. 3. 4. CO2H
O
Lecture 4
O O
OH O O O
1. 2. 3. 4. Ph 5. 6.
CHO
O CH2OH
N
MeO
7. 8. 9. CHO
O
N
Lecture 5
O Me
O
O O MeO OMe
Me
1. 2. Me 3. 4.
O
MeO OCHO Me
O
O Ph
5. 6. Ph S N 7. O
O O O
Lecture 6
CONH2
NO2 CH3
1. O 2. 3. 4. B(OR)3 5. EtNHOH
OH
OH
6. RSO3H 7. 8.
O O
OH
Lecture 7
O O
OAc
1. C 2. 3. 4. Me C O + Me C O
H
O Me Me
5. + OHC
O
Lecture 8
O OOH OH
OOH
O
A. 1. 2. 3. 4. 5.
CHO
Lecture 9
O O
HO Me
Me CO2H
1. CH3CHO 2. 3. 4. CO2H 5. CHO
Me CO2Me
O
OH
CO2H
8. O 9.
6. O 7. O
Lecture 10
O
O OTBS
A. 1. O 2. OHC
O
O MeMe Me
MCPBA
MCPBA
B. NH N OH N O.
Lecture 11
O O O
1. 2. 3. 4.
NHCOCH3 O
S HO
HO O
O
O Me OH
5. 6. O 7.
O
Ph Ph
Lecture 12
OH Me Me
HO OH MeO2C OH HO HO
OH
1. Ph 2 MeO2C 3. 4. 5.
Me Ph MeO2C OH HO HO
H H
O Me
HO H
O
6.
H
Lecture 13
OH OH OH O
OH
1. HO CHO + HO
OH OH OH OH
OH
CO2H
2. 3. HO2C CO2H 4.
OH OH
Lecture 14
1. LAH (inverse addition) 2. LAH 3. LiAlH(OEt)3 4. LiAlH(OEt)3 5. DIBAL, Toluene, -78 oC
Lecture 15
Me
A. 1. NaCNBH3 2. NaCNBH3
OH H H H
Ph O OH N S
B. 1. OEt N
Ar 2. 3. O
N O
O O
OH O Cl H H
H H
H-BH3Na OH
CCl3 NaOH Cl Cl
C.
O O
Lecture 16
OH CO2H OEt
O
1. 2. 3. 4. 5. 6.
OH
7. 8. 9.
NH2 Ph
Br
Lecture 17
Lecture 18
O
H
OH 5.
A. 1. 2. 3. 4. O
N O
H H
OH
Lecture 19
OH
OH O
OH O OH
1. Ph 3. HO OH + H C CH3 4.
2. 3
OEt
S
Lecture 20
OH Cl
1. OH 2. 3. 4. 5. CHO
OH
OTHP O
Br
Me
OH O O
8. 9.
6. 7.
O
Lecture 21
O
NC Me Me
O
1. 2. CH2OH 3. 4. NMe2 5. BnO OH
O
Li OH
Lecture 22
MeO2C CO2Me
N O Me Me
OH
OEt
1. 2. MeO2C 3. Ph 4.
Me
Me
OLi
5. OTBDS 6. 7.
SiMe3
Lecture 23
CO2Me Me O O
CO2Me
CO2Me Me
A. B. C. Ph Et D. E. Me
OH
F. Me
Lecture 24
N N H S
1. 2. N 3.
O N
Ph
OC8H17 SiMe3 O
O
4. 5. 6.
Me3Si OC8H17
Lecture 25
H thexyl H O
thexyl-BH2 B CO-H2O
2.
H2O2/NaOH
H H
Lecture 26
OH
1. (a) A Li/Me3SiCl B. MeCOCl/AlCl3 (b) C.
SiMe3 D. Ph
O
H O Ph
2. (a) (b) (c)
Me3Si SiPh3
Lecture 27
SiMe3
O H
Ph Ph
O
1. 2. 3. S 4. 5. O
O Ph OH COPh
O
OMe H OBn
O
Ph3Sn O
6. 7.
O
O
Lecture 28
N N HO OAc
B. 1. 2. N 3. N 4. 5. AcO CH(CO2Me)2
N N
Ph
Ar Ar
Lecture 29
MeO2C Me
2. 3. Ph 4. Me2N Ph
O O
Ph
5. CO2Et 6. 7.
CN
Lecture 30
CH3 CO2Me
1. CHO 2. F C 3.
3 CHO NEt2 4. NHAc
O
OH OH
5. Ph N N
6. 7.
Ph Ph
Ph
Lecture 31
OH
OH O O O
1. 2. 3. 4.
OH O
O
CO2Me OMe
5. HCONMe2 6. O 7. 8.
OH Et
9. Me OH
Lecture 32
OH Me OH
H
tBu CO2Me
1. 2. 3. (CO)3Cr 4. (CO)3Cr
MeO CO2Me
OMe Cr(CO)3 OH
OH
5. Me CO2Me 6. Ph 7. SnBu3
SiMe3
Lecture 33
O
OH OMe OH H OTMS
NO2
1. Ph 2. 3. 4. 5. CN
H
O OAc
Lecture 34
O O
Br Br O
1. 2. 3. 4. OH
O Br Br
O O
O O
5. 6. 2 O 7.
I
Lecture 35
O
HO O
HO
HO CO2Me
1. 2. Ph 3. 4. 5. OH
OH
NHBn O
H
6. 7.
NHBn
H
O
Lecture 36
Br O
1. O 4.
2. Cl 3.
Br Br Br
Br TsHN
O O
5. 6. 7.
Br Br Br
OH
Lecture 37
O O
NH HN Ph
O
O O
1. 2. 3. 4. BocHN N CO2Me
O O O H
CO2Me
O
Lecture 38
O O O O
N2 2. N2
1. EtO 3. Ph O N N2
H
O
O O O O
4. Ph O N N CO2Me 5. Ph O N OH
H H H
Lecture 39
CO2Et
1. 2. 3. Ph CHO
N
OMe
CN
OMe Ph O
4. 5. P OEt
Ph OEt
Lecture 40
O
O
O OH
1. Me 3. 4.
2. 5.
OH