A Convenient Method for the Preparation of Ellipticine

Abstract

A convenient method for the synthesis of ellipticine is reported. This synthesis is achieved by modifying the processes of Woodward and Sainsburg. The overall yield of this five step synthesis is 12 percent.

Isolation, biological activity and synthesis of the natural product ellipticine and related pyridocarbazoles

“…90 In the C-type category, the early routes employed harsh conditions and were low yielding. 2, 93 Gribble's ketolactam route was the most important progression in this area and easily stands out as the highest yielding synthesis of ellipticine overall (59% over five steps). 100 It has also been shown to be versatile for preparation of both substituted ellipticines and analogues.…”

“…Zee and Su were attracted by the simplicity of Woodward's original route and attempted to adapt the route to overcome the problematic reactions and low yields (Scheme 14). 93 The initial condensation of indole and 3-acetylpyridine was catalysed by HCl instead of zinc chloride, which improved the yield of bisindoyl derivative 65 (81%). Vacuum pyrolysis of 65 gave 67 (50%), which was hydrogenated to give the key intermediate 68 (90%).…”

Design and Synthesis of Ellipticinium Salts and 1,2-Dihydroellipticines with High Selectivities against Human CNS Cancers in vitro

“…2-(2,3,4-Tri-0-acetyl-a-L-arabinopyranosyl)elIipticinium Bromide (22). Under an argon atmosphere a suspension of ellipticine (246 mg, 1.0 mmol), 2,3,4-tri-0-acetyl-/9-L-arabinpyranosyl bromide (678 mg, 2.0 mmol), and cadmium carbonate (258 mg, 1.5 mmol) in dry nitromethane (30 mL) was heated under reflux for 15 min.…”

“…H),5.44-5.43 (m, 1H),4.33 (s, 2 H),3.39 (s, 3 H),2.89 (s, 3 H),2.27 (s, 3 H), 2.00 (s, 3 H),1.80 (s, 3 H); low-resolution FABMS m/z (relative intensity) 505 (M+, 100), 247 (89), 233 (64); highresolution FABMS calcd M+ 505.1975, found 505.1973.2-a-L-Arabinopyranosylellipticinium Bromide (23).A solution of22 (50 mg, 0.085 mmol) in methanol (8 mL) was cooled to 0 °C, saturated with anhydrous ammonia, and stirred at 0 °C for 24 h. The mixture was filtered, and the filtrate was concentrated on a rotary evaporator. The residue was dissolved in methanol (10 mL), concentrated to dryness, and triturated with methylene chloride (20 mL).…”

Recent progress in the chemistry of indole alkaloids and mould metabolites

“…Aristofruticosine, a new alkaloid from A. fructicosa Hook. f., has the novel structure (125), in which the hydroaromatic portion consists of fused pairs of five-and six-membered rings, a ring system that has not previously been encountered in natural or synthetic compounds.7d…”