Synthesis of Eudistomin C

C14H16BrN3O2S
Principal investigator | Tohru Fukuyama |
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Publication year | 2005 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
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FeCl2,
HCl,
Fe
EtOH, H2O
80 °C, 2 h

Pyr,
(CF3CO)2O
CH2Cl2
0 °C, 62% (3 steps)




Boc2O,
DMAP
CH2Cl2
RT, 20 min, 100%

Camphorsulfonic acid
CH2Cl2, MeOH
RT, 30 min, 97%



Me2S
CH2Cl2, CF3CO2H
RT, 30 min, 97%

K2CO3,
PhSH
DMF
RT, 45 min, 94%



- n-BuLi
- ClCO2CH(Cl)CH3
THF
-78 °C to RT, 45 min, 89%

SO2Cl2
CH2Cl2
-78 °C to RT, 35 min

i-Pr2NEt,
AcSH
CH2Cl2
RT, 95% (2 steps)

AcOH
H2O, THF
80 °C, 15 min, 61%

i-Pr2NEt,
MsCl
CH2Cl2
0 °C, 5 min, 98%

K2CO3
MeOH
80 °C, 15 min, 65%

BBr3
CH2Cl2
-78 °C to RT, 2.5 h, 78%
