15.01 Note: show stereochemistry as appropriate
↓ i. BH3; then H2O2, NaOH. ii. PCC.
TM S
220
210
200
190
180
170
↓ Ph3P=CH2
↓ MCPBA
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
0
15.02
↓ H2, Pd-C
↓ H3O+ Cl- (hint...removes a protecting group)
↓ I (MeO)2P(=O)CH2CO2Et + NaH
TMS
220
210
200
1 90
18 0
170
160
150
140
130
120
1 10
10 0
90
80
70
60
50
40
30
20
10
0
15.03
TMS
220
210
200
1 90
18 0
170
160
150
140
130
120
1 10
10 0
90
80
70
60
50
40
30
20
57
184
155
10
0
15.04
TMS
220
210
200
1 90
18 0
170
160
150
140
130
120
1 10
10 0
90
80
70
60
50
40
154
30
20
10
0
16.01
↓ H2O, H2SO4
↓ H2CrO4, H2O
TMS
220
210
200
1 90
18 0 170
160
150
140
130
120 1 10
10 0
↓ I HC≡CH + NaNH2
X w D 2O
90
80
70
60
50
40
30
20
10
0
16.02
TMS
220
210
200
1 90
18 0 170
160
150
140
130
120 1 10
10 0
90
80
70
60
50
40
30
20
10
0
↓ H+ (cat.) + C3H8O2 (note: C3H8O2 shows two peaks at ~3300 cm-1 in the IR)
↓ PCC
↓ I NaNH2 + I Ø3P + C5H9Br (note: C5H9Br shows 3 peaksLKK in the 13C NMR)
↓ H3O+ Cl- (removes a protecting group)
126
16.03
84
↓ i. H+ (cat.) + HOCH2CH2OH; ii. BH3; H2O2, NaOH
↓ i. PCC; ii. (CH3)2CHMgBr
TMS
220
210
200
1 90
18 0
170
160
150
140
130
120
1 10
10 0
90
80
70
↓ H+ (cat.) + MeOH (solvent AND reactant)
60
50
40
30
20
10
16.03.3
0
16.03.4
16.04
Write a detailed, stepwise mechanism for 16.03.3 → 16.03.4 (see previous problem)
16.05
TMS
220
210
200
1 90
18 0
170
160
150
140
130
120
1 10
10 0
90
80
70
60
50
40
30
20
10
0