Concise Large-Scale Synthesis of Psilocin and Psilocybin, Principal Hallucinogenic Constituents of “Magic Mushroom”

• Published in: Journal of natural products (Washington, D.C.) Vol. 66; no. 6; pp. 885 - 887
• Main Authors: Shirota, Osamu, Hakamata, Wataru, Goda, Yukihiro
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.06.2003; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Agaricales - chemistry; Biological and medical sciences; Chemistry; Chemistry, Medicinal; Combinatorial Chemistry Techniques; Exact sciences and technology; General pharmacology; Hallucinogens - chemical synthesis; Hallucinogens - chemistry; Hallucinogens - pharmacology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Life Sciences & Biomedicine; Medical sciences; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Organic chemistry; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Preparations and properties; Psilocybin - analogs & derivatives; Psilocybin - chemical synthesis; Psilocybin - chemistry; Psilocybin - pharmacology; Science & Technology; VON PSILOCYBIN; LIQUID-CHROMATOGRAPHY; BAEOCYSTIS; ANALOGS; UND PSILOCIN; DRUGS; CHROMATOGRAPHY-MASS-SPECTROMETRY; Nitrogen heterocycle; Psychotropic; Hallucinogen; Tertiary amine; Bicyclic compound; Organic phosphate; Phenols; Aromatic compound; Chemical synthesis; Phosphorus Organic compounds
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np030059u

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.