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Named reactions

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Promothiocin A

Chemical structure of Promothiocin_A
C36H37N11O8S2
Author Christopher J. Moody
Publication year 2000
Synthesis type Total synthesis
Number of steps 31 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
+
Chemical structure
Rh2(OAc)4
CHCl3
Reflux, 6.5 h, 71 %
Chemical structure
I2, Ph3P, Et3N
CH2Cl2
RT, 56 %

See the Robinson-Gabriel Synthesis
Chemical structure
H2, Pd/C
1 atm
MeOH
RT, 4 h, 100 %
Chemical structure
+
Chemical structure
N-Methylmorpholine
THF
-10 to 0 °C, 60 min, 87 %
Chemical structure
LiOH
THF, H2O
RT, ON, 93 %
Chemical structure
+
Chemical structure
ClCO2i-Bu, N-Methylmorpholine
THF
0 °C to RT, 90 min, 84 %
Chemical structure
AcCl
EtOH
RT, ON, 100 %
Chemical structure

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Part 2 of 3
Chemical structure
+
Chemical structure
Rh2(OAc)4
CHCl3
Reflux, ON, 80 %
Chemical structure
I2, Ph3P, Et3N
CH2Cl2
RT, ON, 70 %

See the Robinson-Gabriel Synthesis
Chemical structure
LiOH
MeOH, H2O
RT, 5 h, 95 %
Chemical structure
+
Chemical structure
ClCO2Et, Et3N
THF
0 °C to RT, ON, 77 %

See the Claisen Condensation
Chemical structure
NH4OAc
Dean-Stark
PhH, AcOH
Reflux, 24 h, 85 %
Chemical structure
+
Chemical structure
EtOH
50 °C, ON, 83 %

See the Bohlmann-Rahtz Pyridine Synthesis
Chemical structure
LiOH
THF, H2O
RT to 45 °C, 2.5 d, 92 %
Chemical structure
  1. ClCO2Et, Et3N
  2. NH3, H2O
THF
-10 °C to RT, 2 h, 85 %
Chemical structure
Reagent structure
PhH
Reflux, 5 h, 59 %
Chemical structure
+
Chemical structure
KHCO3
THF
-3 °C, 16 h

See the Hantzsch Thiazole Synthesis
Chemical structure
(CF3CO)2O, 2,6-Lutidine
THF
0 °C, 3 h, 72 % (2 steps)
Chemical structure
LiOH
THF, H2O
RT, ON, 94 %
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
ClCO2i-Bu, N-Methylmorpholine
THF
0 °C, 90 min, 69 %
Chemical structure
LiOH
THF, H2O
RT, ON, 94 %
Chemical structure
EDC, C6F5OH
CH2Cl2
0 °C to RT, ON
Chemical structure
HCl
Dioxane
RT, 3.5 h
Chemical structure
Et3N
CHCl3
RT, 4 d, 55 % (3 steps)
Chemical structure
BCl3, Me2S
CH2Cl2
0 °C to RT, ON, 39 %
Chemical structure
IBX
DMSO
RT, 4.5 h, 81 %
Chemical structure
NaClO2, NaH2PO4, 2-Methyl-2-butene
t-BuOH, H2O
RT, 5 h, 70 %

See the Pinnick-Lindgren Oxidation
Chemical structure
+
Chemical structure
EDC
CH2Cl2
RT, ON, 50 %
Chemical structure
n-Bu4N+ F-
THF
RT, 90 min, 57 %
Chemical structure
MsCl, Et3N
CH2Cl2
RT, 60 min
Chemical structure
Et3N
CH2Cl2
RT, ON, 59 % (2 steps)
Chemical structure

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