Synthesis of Lysergic Acid

Structure of Lysergic Acid

C16H16N2O2

Principal investigatorRobert B. Woodward
Publication year1954
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
H2, Ni (Raney), NaOH
H2O
RT, 20-30 h
intermediate structure
BzCl, NaOH
H2O
RT to 40 °C, , 70% (2 steps)
intermediate structure
SOCl2
RT to reflux, 45-55 min
intermediate structure
AlCl3
CS2
Reflux, 60 min, 77% (2 steps)
intermediate structure
PyrHBr3
AcOH
40-60 °C, 30 min, 69%
intermediate structure + intermediate structure
PhH
Reflux, 21 h, 71%
intermediate structure
HCl
H2O
37 °C, 5 d, 77%
intermediate structure
NaOMe
MeOH
-10 °C, 10 min, 69%
intermediate structure
Ac2O
RT, 5 min, 82%
intermediate structure
  1. NaBH4
  2. HCl
MeOH, H2O
RT, 2 h, 79%
intermediate structure
SOCl2
SO2
RT, 6 h
intermediate structure
NaCN, HCN
0-10 °C, 30 min, 54% (2 steps)
intermediate structure
H2SO4
MeOH, H2O
100 °C, 24 h, 53%
intermediate structure
  1. KOH
  2. Ni (Raney)
  3. Na3AsO4.12H2O
H2O
Reflux, 20.5 h, 30%
intermediate structure