Synthesis of Dibromophakellstatin

Structure of Dibromophakellstatin

C11H10Br2N4O2

Principal investigatorDaniel Romo
Publication year2003
Synthesis typeTotal
Number of steps 16 (linear)
References
Part 1 of 1
intermediate structure
  1. TMS2NK
  2. ClCO2Bn
THF
-78 °C, 6 h, 70%
intermediate structure
  1. TMS2NK
  2. PhSeBr
THF
-78 °C, 55 min, 73%
intermediate structure
DMDO
CH2Cl2
-78 to 0 °C, 2 h, 93%
intermediate structure
SeO2
Dioxane
Reflux, 12 h, 65%
intermediate structure
NaBH4
MeOH
-40 °C, 15 min, 88%
intermediate structure
KOt-Bu
t-BuOH
RT, ON
intermediate structure
Ac2O, Pyr
CH2Cl2
RT, ON, 58% (2 steps)
intermediate structure
H2, Pd/C
EtOAc, EtOH
RT, 30 min
intermediate structure
Phosgene, BnOC(O)NHOH, DMAP
CH2Cl2, DMF
0 °C to RT, ON, 77% (2 steps)
intermediate structure
NH3
MeOH
0 °C, 30 min, 90%
intermediate structure
DIAD, Ph3P
THF
RT to Reflux, 3 h
intermediate structure
NH3
MeOH
0 °C, 5 min
intermediate structure
TiCl3, KOAc
THF, H2O
23 °C, , 53% (3 steps)
intermediate structure
PhI(O2CCF3)2, Pyr
MeCN
RT, 3 h
intermediate structure
H2, Pd/C
MeOH
RT, 60 min, 50% (2 steps)
intermediate structure
NBS
THF
RT, 60 min, 69%
intermediate structure