Synthesis of Dibromophakellstatin

Structure of Dibromophakellstatin

C11H10Br2N4O2

Principal investigatorDaniel Romo
Publication year2003
Synthesis typeTotal
Number of steps 16 (linear)
References
J. Am. Chem. Soc. 2003, 125, 6344. Org. Lett. 2002, 4, 2645.
Part 1 of 1
intermediate structure
  1. TMS2NK
  2. ClCO2Bn
THF
-78 °C, 6 h, 70%
See the Claisen Condensation
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
1 atm
EtOAc, EtOH
RT, 30 min
intermediate structure
BnOC(O)NHOH, DMAP, Phosgene
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
See the Mitsunobu Reaction
intermediate structure
NH3
MeOH
0 °C, 5 min
intermediate structure
KOAc, TiCl3
H2O, THF
23 °C, 53% (3 steps)
intermediate structure
Pyr, PhI(O2CCF3)2
Dark
MeCN
RT, 3 h
See the Hofmann Rearrangement
intermediate structure
H2, Pd/C
1 atm
MeOH
RT, 60 min, 50% (2 steps)
intermediate structure
NBS
THF
RT, 60 min, 69%
intermediate structure
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