Synthesis of Dibromophakellstatin

Structure of Dibromophakellstatin

C11H10Br2N4O2

Principal investigatorDavid J. Austin
Publication year2004
Synthesis typeTotal
Number of steps 8 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
CH2Cl2
RT, ON, 49%
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 2 h
intermediate structure
MsCl, DBU
CH2Cl2
0 °C to RT, ON, 67% (2 steps)
intermediate structure
PhI(OAc)2, TMSN3, n-Bu4N+ I-
CH2Cl2
-30 °C to RT, ON, 41%
"Also isolated was the C10-epimer (7 % yield)."
intermediate structure
H2, Pd/C
MeOH
RT, ON, 75%
intermediate structure
TCDI, Imidazole
MeCN
50 °C, , 69%
intermediate structure
H2O2, NH3
DMF, H2O
RT, 4 h, 91%
intermediate structure
NBS
THF
RT, ON, 30%
intermediate structure