Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin
نویسندگان
چکیده
An improved procedure to accomplish the O-phosphorylation of 4-hydroxy-N,N-dimethyltryptamine (psilocin 5) is reported that utilizes reaction between the O-lithium salt of 5 and tetra-Obenzylpyrophosphate. The O-benzyl groups were removed by catalytic hydrogenation over palladium on carbon to afford N,N-dimethyl-4-phosphoryloxytryptamine (psilocybin, 1). In view of difficulties encountered in the preparation of 1, it is suggested that 4-acetoxy-N,N-dimethyltryptamine (2) may be a useful alternative for pharmacological studies. The latter was obtained following catalytic O-debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.
منابع مشابه
Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom".
The concise large-scale syntheses of psilocin (1) and psilocybin (2), the principal hallucinogenic constituents of "magic mushroom", were achieved without chromatographic purification. The key step in the synthesis of 2 was the isolation of the dibenzyl-protected intermediate (7) as a zwitterionic derivative (8), which was completely identified by means of 2D NMR analyses.
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