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Acetylkomaroidine (1c). Fractions 8-15 were combined. Solvent was distilled off. The residual was crystallized from ethanol:acetone to afford 1c (34 mg), mp 229-230°C.Extraction and separation of the total bases from N. komarovii has been described in detail [8,9]. The benzene part of the total bases was separated by chromatography over a silica-gel column with elution by CHCl 3 :CH 3 OH (20:1, 10:1, 4:1). Fractions (15-20 mL) were collected.Komaroidine (1b). Fractions 14-16 were combined and separated by chromatography over a silica-gel column with elution by CHCl 3 :CH 3 OH (10:1). Fractions (8-10 mL) were collected. Fractions 17-23 were combined and worked up by crystallization from ethanol:acetone to afford 1b (56 mg), mp 207-208°C.Acetylkomaroidine (1c). Fractions 11-16 were combined and worked up by crystallization from ethanol:acetone to afford 1c (51 mg), mp 229-230°C.Hydrolysis of 1c. Komaroidine. Base 1c (0.05 g) was dissolved in HCl (5 mL, 1 N) and heated at 90°C for 2 h. After the reaction was complete, the solution was cooled, made basic with KOH solution (10%), and extracted with CHCl 3 . Solvent was distilled off. The residual was crystallized from acetone:ethanol to afford komaroidine (0.027 g), mp 207-208°C.Acetylation of Komaroidine (Acetylkomaroidine). A mixture of 1b (0.04 g), pyridine (1 mL), and acetic anhydride (1 mL) was left at room temperature for 5 d. After the reaction was complete, the excesses of anhdyride and pyridine were removed in vacuo. The dry residual was treated with water (2 mL) and made basic with conc. aqueous NH 3 . The product was extracted with ether. The ether extract was dried over anhydrous Na 2 SO 4 . Solvent was distilled off. The residual was crystallized from acetone:ethanol to afford N-acetylkomaroidine (0.031 g), mp 229-230°C.Synthesis of Komaroidine. A mixture of tryptamine hydrochloride (1 g, 0.005 mol) in water (15 mL), ethanol (25 mL), H 2 SO 4 (3 mL, 2 N), and butyraldehyde (3 mL) was gradually heated to boiling on a sand bath and held at this temperature for 5 h. The alcohol was distilled off in vacuo. The solution was made basic with conc. aqueous NH 3 . The product was extracted with CHCl 3 . The CHCl 3 was distilled off. The solid was crystallized from acetone:alcohol to afford 1b (0.91 g), mp 207-208°C.Synthesis of Schobericine. Schobericine was synthesized by condensation of serotonin and butyraldehyde by the method described above for the synthesis of komaroidine to afford 1a (0.87 g), mp 193-194°C.

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