Synthesis of Eudistomin C

Structure of Eudistomin C

C14H16BrN3O2S

Principal investigatorTohru Fukuyama
Publication year2005
Synthesis typeTotal
Number of steps 18 (linear)
References
Part 1 of 1
intermediate structure
  1. H2SO4
  2. KI
  3. NaNO2
H2O, MeCN
0 °C to RT, 15 min
intermediate structure
HCl, Fe, FeCl2
EtOH, H2O
80 °C, 2 h
intermediate structure
Pyr, (CF3CO)2O
CH2Cl2
0 °C, , 62% (3 steps)
intermediate structure + intermediate structure
DEAD, Ph3P
PhH
5 °C to RT, 15 min, 90%
intermediate structure
Et3N, Pd(OAc)2, Et3NBn+ Cl-
DMF
80 °C, 30 min, 66%
See the Heck Coupling
intermediate structure
DMAP, Boc2O
CH2Cl2
RT, 20 min, 100%
intermediate structure
Camphorsulfonic acid
CH2Cl2, MeOH
RT, 30 min, 97%
intermediate structure + intermediate structure
DEAD, Ph3P
PhH
5 °C to RT, 15 min, 100%
intermediate structure
Me2S
CH2Cl2, CF3CO2H
RT, 30 min, 97%
intermediate structure
K2CO3, PhSH
DMF
RT, 45 min, 94%
intermediate structure + intermediate structure
Cl2CHCO2H
PhMe
0 °C, 15 min, 100%
intermediate structure
  1. n-BuLi
  2. ClCO2CH(Cl)CH3
THF
-78 °C to RT, 45 min, 89%
intermediate structure
SO2Cl2
CH2Cl2
-78 °C to RT, 35 min
intermediate structure
i-Pr2NEt, AcSH
CH2Cl2
RT, , 95% (2 steps)
intermediate structure
AcOH
H2O, THF
80 °C, 15 min, 61%
intermediate structure
i-Pr2NEt, MsCl
CH2Cl2
0 °C, 5 min, 98%
intermediate structure
K2CO3
MeOH
80 °C, 15 min, 65%
intermediate structure
BBr3
CH2Cl2
-78 °C to RT, 2.5 h, 78%
intermediate structure