Synthesis of Methoxatin

Structure of Methoxatin

C14H6N2O8

Principal investigatorSteven M. Weinreb
Publication year1981
Synthesis typeTotal
Number of steps 14 (linear)
References
J. Org. Chem. 1981, 46, 4317.
Part 1 of 1
intermediate structure
  1. (CH2NMe2)2 , n-BuLi
  2. CO2
Hexane(s)
RT, 18 h, 66%
intermediate structure
  1. ClCO2Et , Et3N
  2. NaN3
PhMe
Reflux
See the Curtius Rearrangement
intermediate structure
  1. KOH
  2. HCl
H2O
60% (2 steps)
intermediate structure
Cl3CCH(OH)2, NH2OH.HCl, Na2SO4
H2O
50-60 °C
See the Sandmeyer Isatin Synthesis
intermediate structure
PPA
100 °C, 10 min, 70% (2 steps)
See the Sandmeyer Isatin Synthesis
intermediate structure + intermediate structure
KOH
H2O
95 °C, 6 h
See the Aldol Condensation
intermediate structure
H2SO4
MeOH
Reflux, 50% (2 steps)
See the Fischer-Speier Esterification
intermediate structure
NBS
CCl4
Reflux, 3 h, 90%
See the Wohl-Ziegler Reaction
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- , Pyr
  2. NaBH4 , MeOH
H2O
-10 °C, 70%
See the Japp-Klingemann Reaction
intermediate structure
H2, HCl, Pd/C
1 atm
MeOH
62%
See the Leimgruber-Batcho Indole Synthesis
intermediate structure
HNO3, AgO
THF
RT, 10 min, 60%
intermediate structure
LiOH
H2O, THF
RT, 5 h, 75%
intermediate structure
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