Synthesis of Promothiocin A
C36H37N11O8S2
| Principal investigator | Christopher J. Moody |
|---|---|
| Publication year | 2000 |
| Synthesis type | Total |
| Number of steps | 31 (3 parts) |
| References |
Part 1 of 3
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+
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Rh2(OAc)4
CHCl3
Reflux, 6.5 h, 71 %
Pd/C,
H2
1 atm
MeOH
RT, 4 h, 100%
+
N-Methylmorpholine
THF
-10 to 0 °C, 60 min, 87%
LiOH
H2O, THF
RT, ON, 93%
+
ClCO2i-Bu,
N-Methylmorpholine
THF
0 °C to RT, 90 min, 84%
AcCl
EtOH
RT, ON, 100%
Part 2 of 3
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+
+
+
+
Rh2(OAc)4
CHCl3
Reflux, ON, 80%
LiOH
H2O, MeOH
RT, 5 h, 95%
+
NH4OAc
Dean-Stark
AcOH, PhH
Reflux, 24 h, 85%
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LiOH
H2O, THF
RT to 45 °C, 2.5 d, 92%
- Et3N , ClCO2Et
- H2O , NH3
THF
-10 °C to RT, 2 h, 85%
PhH
Reflux, 5 h, 59%
+
(CF3CO)2O,
2,6-Lutidine
THF
0 °C, 3 h, 72% (2 steps)
LiOH
H2O, THF
RT, ON, 94%
Part 3 of 3
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+
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N-Methylmorpholine,
ClCO2i-Bu
THF
0 °C, 90 min, 69%
LiOH
H2O, THF
RT, ON, 94%
C6F5OH,
EDC
CH2Cl2
0 °C to RT, ON
HCl
Dioxane
RT, 3.5 h
Et3N
CHCl3
RT, 4 d, 55% (3 steps)
BCl3,
Me2S
CH2Cl2
0 °C to RT, ON, 39%
IBX
DMSO
RT, 4.5 h, 81%
+
EDC
CH2Cl2
RT, ON, 50%
n-Bu4N+ F-
THF
RT, 90 min, 57%
MsCl,
Et3N
CH2Cl2
RT, 60 min
Et3N
CH2Cl2
RT, ON, 59% (2 steps)