Synthesis of Acromelobinic Acid

Structure of Acromelobinic Acid

C9H10N2O5

Principal investigatorMaciej Adamczyk
Publication year2001
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
mCPBA
CHCl3
RT, 15 h, 78%
intermediate structure
Ac2O
Reflux, 3 h
intermediate structure
NaOMe
MeOH
0 & deg;C, 10 min, 60% (2 steps)
intermediate structure
MeI, Ag2CO3
CHCl3
RT, 5 d, 93%
intermediate structure
AIBN, NBS
CCl4
Reflux, 45 min, 77%
intermediate structure
HMTA
AcOH, H2O
Reflux, 60 min, 34%
intermediate structure + intermediate structure
1,1,3,3-Tetramethylguanidine
THF
0 °C to RT, 6 h, 66%
"Also isolated was the E-isomer (10 % yield)."
intermediate structure
H2
MeOH
RT, , 93%
intermediate structure
LiOH
H2O, THF
RT, 60 min
intermediate structure
TMSI
CHCl3, MeOH
Reflux, 19 h, 88% (2 steps)
intermediate structure