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Choong TC, Shough HRT.
“The Synthesis of Lysergic Acid Derivatives from Elymoclavine”.
Tetrahedron Letters. 1977;1977(19):1627-28.
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Abstract
The synthesis of lysergic acid methyl ester (4; R=OCH3) and related compounds including LSD (4, R=NEt2) from the ergot alkaloid, elymoclavine (1), is reported. (2) Has been prepared previously by oxidation of (1) with MnOz/MeOH. The cyanide-catalyzed oxidation of (2) with MnOz/MeoH yielded (3; R=OCH3), which with Zn/AcOH gave (4; R=OCH3). (3 and 4; R=NEtz) were prepared by replacing MeOH with the appropriate amine in the oxidation of (2). Attempts to prepare lysergic acid (4; R=OH) by AgO oxidation of (2) were unsuccessful.
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