Synthesis of Methoxatin

Structure of Methoxatin

C14H6N2O8

Principal investigatorSteven M. Weinreb
Publication year1981
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
  1. n-BuLi
  2. (CH2NMe2)2
  3. CO2
Hexane(s)
RT, 18 h, 66%
intermediate structure
  1. ClCO2Et
  2. Et3N
  3. NaN3
PhMe
Reflux
intermediate structure
  1. KOH
  2. HCl
H2O
60% (2 steps)
intermediate structure
Cl3CCH(OH)2, NH2OH.HCl, Na2SO4
H2O
50-60 °C
intermediate structure
PPA
100 °C, 10 min, 70% (2 steps)
intermediate structure + intermediate structure
KOH
H2O
95 °C, 6 h
intermediate structure
H2SO4
MeOH
Reflux, , 50% (2 steps)
intermediate structure
NBS
CCl4
Reflux, 3 h, 90%
intermediate structure
HNO3
H2SO4
-20 °C, 1.5 min, 60%
intermediate structure + intermediate structure
NaH
THF
RT, 2 h, 92%
intermediate structure
  1. PhN2+ BF4-
  2. Pyr
  3. NaBH4
  4. MeOH
H2O
-10 °C, , 70%
intermediate structure
H2, Pd/C, HCl
MeOH
62%
intermediate structure
AgO, HNO3
THF
RT, 10 min, 60%
intermediate structure
LiOH
THF, H2O
RT, 5 h, 75%
intermediate structure