Synthesis of Lysergic Acid

Structure of Lysergic Acid

C16H16N2O2

Principal investigatorWolfgang Oppolzer
Publication year1981
Synthesis typeTotal
Number of steps 11 (linear)
References
Helv. Chim. Acta 1981, 64, 478. US Patent 4,491,664A
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
See the Mannich Reaction
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%
See the Diels-Alder Reaction
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
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