Synthesis Laboratory Lysergic acid is generally produced by
hydrolysis of natural lysergamides, but can also be synthesized in the laboratory by a complex
total synthesis, for example by
Robert Burns Woodward's team in 1956. An
enantioselective total synthesis based on a
palladium-catalyzed domino
cyclization reaction has been described in 2011 by Fujii and Ohno. Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at ) forms anhydrous lysergic acid.
Biosynthesis The biosynthetic route is based on the
alkylation of the amino acid
tryptophan with
dimethylallyl diphosphate (
isoprene derived from 3
R-
mevalonic acid) giving 4-dimethylallyl--tryptophan which is
N-methylated with
S-adenosyl--methionine. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic
isomerization yields -(+)-lysergic acid.
Illicit production Lysergic acid manufactured by clandestine chemists to use in the illictic synthesis of
LSD is produced using
Ergotamine tartrate or
Ergometrinine.
Isomers Lysergic acid is a
chiral compound with two
stereocenters. The
isomer with inverted configuration at carbon atom 8 close to the
carboxyl group is called
isolysergic acid. Inversion at carbon 5 close to the
nitrogen atom leads to
-lysergic acid and
-isolysergic acid, respectively. ==Society and culture==