Synthesis of Lysergic Acid

C16H16N2O2
Principal investigator | Robert B. Woodward |
---|---|
Publication year | 1954 |
Synthesis type | Total |
Number of steps | 14 (linear) |
References |
Part 1 of 1
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H2,
NaOH,
Ni (Raney)
200-270 atm
H2O
RT, 20-30 h


SOCl2
RT to reflux, 45-55 min


PyrHBr3
hv
AcOH
40-60 °C, 30 min, 69%


PhH
Reflux, 21 h, 71%

HCl
H2O
37 °C, 5 d, 77%


Ac2O
RT, 5 min, 82%

- NaBH4
- HCl
H2O, MeOH
RT, 2 h, 79%

SOCl2
SO2
RT, 6 h

HCN,
NaCN
0-10 °C, 30 min, 54% (2 steps)

H2SO4
H2O, MeOH
100 °C, 24 h, 53%

Ni (Raney, Deactivated),
KOH,
Na3AsO4.12H2O
H2O
Reflux, 20.5 h, 30%
