Chem 212 Provide synthesis for the following molecules from the given starting material.

Synthesis problems 3

Cl OMe OMe

1. HNO3, H2SO4 +
H2N 2. Cl2, FeCl3
3. SnCl2, H3O+ O O
4. Ac2O O
5. AlCl3,
Cl O O
O
6. NH2NH2, HO-, heat O O O O
NH2 O + +
O O

Br O
1. Br2, FeBr3 O
SO3H
2. HNO3, H2SO4
3. SO3, H2SO4 HO H O
4. SnCl2, H3O+
NO2 HO
5. neutralize
+
Br
1. heat
2. NaBH4, MeOH
OH 1. SO3, H2SO4 3. Br2, H2O
2. NaOH, 300 °C
3. H3O+
4. HNO3, H2SO4 O
O 1. NaOMe, O O
OH O
O OMe (Michael) OMe
O2N O
O 2. LDA, -78 oC
1. AlCl3, Cl (intramolecular Claisen)
3. NaOMe, MeI
2. HBr, peroxides 4. NaOMe, O
3. AlCl3 O
4. HNO3, H2SO4 (Michael) O
5. NaBH4, MeOH o
5. LDA, -78 C(aldol)
O
O
H H
1. NaNH2
2. bromobutane
3. NaNH2
4. bromo propane
5. Li, NH3
OH OH
+

1. AlCl3, Cl
2. Et3SiH, TFA O

O
O
HO H
1. LDA 1. AlCl3, Cl
2. bromopropane
3. NaBH4, MeOH 2. HBr, peroxides
3. AlCl3

O
O
O 1. LDA
2. CH2O O O
3. NaH
O 1. EtOH, H+ (forms ester) O O
4. EtBr
2. NaOEt (Claisen)
OH 3. H3O+ (decarboxylation) OEt O
4. NaH
5. 1,2-dibromoethane
O
6. LDA, -78 oC (forms cyclopentanone) Br
H 11. NaOMe, 3-buten-2-one (Michael)
1. NaNH2, NH3
O HO O
2. OH
Br O Br H
H+ catalyst
3. Li, NH3
4. H3O+