Synthesis of Lysergic Acid

Structure of Lysergic Acid

C16H16N2O2

Principal investigatorWolfgang Oppolzer
Publication year1981
Synthesis typeTotal
Number of steps 11 (linear)
References
Part 1 of 1
intermediate structure
Ph3P, CBr4
DMF
RT, 30 min, 97%
See the Appel Reaction
intermediate structure
n-Bu3P
PhH
Reflux, 2 h, 100%
intermediate structure
Special reagent
NaH
DMSO
RT to 75 °C, 16 h, 62%
See the Wittig Reaction
intermediate structure
NaOH
MeOH
Reflux, 90 min, 95%
intermediate structure
Me2NH, CH2O
AcOH
RT, 2 h
intermediate structure
Special reagent
MeNO2
THF
RT, 5 h, 48% (2 steps)
intermediate structure
  1. NaOMe , NH2OMe.HCl
  2. TiCl3 , NH4OAc , H2O
MeOH
10 to 20 °C, 2 h, 64%
See the Nef Reaction
intermediate structure
1,2,4-Trichlorobenzene
200 °C, 5 h, 67%
intermediate structure
FSO3Me
CH2Cl2
RT, 18 h
intermediate structure
Al(Hg)
H2O, THF
0-5 °C, 18 h
intermediate structure
KOH
EtOH, H2O
Reflux, 60 min, 33% (3 steps)
intermediate structure