Synthesis of Lysergic Acid

Structure of Lysergic Acid

C16H16N2O2

Principal investigator	Robert B. Woodward
Publication year	1954
Synthesis type	Total
Number of steps	14 (linear)
References	J. Am. Chem. Soc. 1956, 78, 3087. J. Am. Chem. Soc. 1954, 76, 5256.

Part 1 of 1

intermediate structure

H2, NaOH, Ni (Raney)

200-270 atm

H2O

RT, 20-30 h

intermediate structure

BzCl, NaOH

H2O

RT to 40 °C, 70% (2 steps)

See the Schotten-Baumann Reaction

intermediate structure

SOCl2

RT to reflux, 45-55 min

intermediate structure

AlCl3

CS2

Reflux, 60 min, 77% (2 steps)

See the Friedel-Crafts Acylation

intermediate structure

PyrHBr3

hv

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%

See the Aldol Condensation

intermediate structure

Ac2O

RT, 5 min, 82%

intermediate structure

NaBH4
HCl

H2O, MeOH

RT, 2 h, 79%

intermediate structure

SOCl2

SO2

RT, 6 h

intermediate structure

HCN, NaCN

0-10 °C, 30 min, 54% (2 steps)

intermediate structure

H2SO4

H2O, MeOH

100 °C, 24 h, 53%

intermediate structure

Ni (Raney, Deactivated), KOH, Na3AsO4.12H2O

H2O

Reflux, 20.5 h, 30%

intermediate structure

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