Synthesis of Dibromophakellstatin

C11H10Br2N4O2
Principal investigator | Daniel Romo |
---|---|
Publication year | 2003 |
Synthesis type | Total |
Number of steps | 16 (linear) |
References |
Part 1 of 1


- TMS2NK
- PhSeBr
THF
-78 °C, 55 min, 73%

DMDO
CH2Cl2
-78 to 0 °C, 2 h, 93%

SeO2
Dioxane
Reflux, 12 h, 65%

NaBH4
MeOH
-40 °C, 15 min, 88%

KOt-Bu
t-BuOH
RT, ON

Ac2O,
Pyr
CH2Cl2
RT, ON, 58% (2 steps)

H2,
Pd/C
1 atm
EtOAc, EtOH
RT, 30 min

BnOC(O)NHOH,
DMAP,
Phosgene
CH2Cl2, DMF
0 °C to RT, ON, 77% (2 steps)

NH3
MeOH
0 °C, 30 min, 90%


NH3
MeOH
0 °C, 5 min

KOAc,
TiCl3
H2O, THF
23 °C, 53% (3 steps)


H2,
Pd/C
1 atm
MeOH
RT, 60 min, 50% (2 steps)

NBS
THF
RT, 60 min, 69%
