Synthesis
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 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 2 mmHg or 270 Pa) forms anhydrous lysergic acid. The biosynthetic route is based on the alkylation of the amino acid tryptophan with dimethylallyl diphosphate (isoprene derived from 3R-mevalonic acid) giving 4-dimethylallyl-L-tryptophan which is N-methylated with S-adenosyl-L-methionine. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic isomerization yields D-(+)-lysergic acid.
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