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Pactamycin
| Author | Stephen Hanessian |
|---|---|
| Publication year | 2011 |
| Synthesis type | Total synthesis |
| Number of steps | 35 (linear) |
| Reference |
Browse hundreds of other total syntheses.
Part 1 of 1
p-MeOBzCl, Et3N
CH2Cl2
RT, 2 h, 64 %
RT, 2 h, 64 %
SOCl2
MeCN
0 °C to RT, 10 h, 85 %
0 °C to RT, 10 h, 85 %
+ 
TESOTf, 2,6-Lutidine
CH2Cl2
0 °C to RT, 2 h, 67 % (2 steps)
0 °C to RT, 2 h, 67 % (2 steps)
i-Bu2AlH
CH2Cl2
-78 °C
-78 °C
O3, Me2S
CH2Cl2
-78 °C to RT, ON, 84 %
-78 °C to RT, ON, 84 %
Cl3CCOCl, Pyr
CH2Cl2
RT, 8 h, 89 %
RT, 8 h, 89 %
H2O2, NaOH
CH2Cl2, MeOH, H2O
0 °C, 2 h, 75 %
See the Michael Addition
Also isolated was the TES-deprotected product (16 % yield).
0 °C, 2 h, 75 %
See the Michael Addition
Also isolated was the TES-deprotected product (16 % yield).
Tf2O, Pyr
CH2Cl2
-78 to 0 °C, 60 min
-78 to 0 °C, 60 min
n-Bu4N+ N3-
4 Å MS
PhMe
RT, 3 d, 86 % (2 steps)
4 Å MS
RT, 3 d, 86 % (2 steps)
CF3CO2H
MeCN, H2O
0 °C, 4 h, 93 %
0 °C, 4 h, 93 %
n-Bu4N+ F-
THF
0 °C to RT, 90 min, 95 %
0 °C to RT, 90 min, 95 %
K2CO3
MeOH
0 °C to RT, 60 min, 87 % (2 steps)
0 °C to RT, 60 min, 87 % (2 steps)
TBDPSCl, Et3N, DMAP
CH2Cl2
0 °C to RT, 4 h, 96 %
0 °C to RT, 4 h, 96 %
Tf2O, Pyr
CH2Cl2
-78 to 0 °C, 60 min, 96 %
-78 to 0 °C, 60 min, 96 %
+ 
Yb(OTf)3
PhMe
80 °C, 9 h, 81 %
The yield was 91 % brsm.
80 °C, 9 h, 81 %
The yield was 91 % brsm.
HCl
THF, H2O
0 °C to RT, 14 h, 63 %
The yield was 83 % after two cycles.
0 °C to RT, 14 h, 63 %
The yield was 83 % after two cycles.
TASF
CH2Cl2
0 °C to RT, 60 min, 95 %
0 °C to RT, 60 min, 95 %
2,2-Dimethoxypropane, Camphorsulfonic acid
CH2Cl2
0 °C to RT, 2 h, 86 %
0 °C to RT, 2 h, 86 %
ClCO2CCl3, Et3N
Activated charcoal
THF
-46 °C, 15 min, 89 %
Activated charcoal
-46 °C, 15 min, 89 %
Me2NH
-46 °C to RT, 97 %
i-Bu2AlH
CH2Cl2
-78 °C, 90 min, 90 %
-78 °C, 90 min, 90 %
NaIO4
THF, H2O
RT, 3 h, 80 % (2 steps)
RT, 3 h, 80 % (2 steps)
CF3CO2H
MeCN, H2O
0 °C to RT, 45 min, 85 %
0 °C to RT, 45 min, 85 %
+ 
K2CO3
DMA
RT, 70 min, 96 %
RT, 70 min, 96 %
H2, Lindlar Catalyst
1 atm
MeOH, EtOH
RT, 3 h, 85 %
1 atm
RT, 3 h, 85 %
