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Experimental Section for the Transformation of Molecule 41 to Sceptrin 1


To begin the synthesis of sceptrin 1 from chloroketone 41, an aminoimidazole formation was performed: Reacting 41 (350 mg, 0.573 mmol) with sodium diformamide ( 300 mg, 3.157 mmol) at 35¡C for 40 hours caused an SN2 reaction at the chlorinated carbon.

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The solvent was then removed in vacuo and the product washed with water (30 mL) and CH2Cl2 (30 mL). The resulting formamide 32 (400 mg) was dissolved in methanol (30 mL) with aqueous HCl (3 mL). This solution was stirred at room temperature for 16 hours, which hydrolyzed the formamide.

Again, the solvent was removed in vacuo and this time the resulting compound was dissolved in water (10 mL) with cyanamide (260 mg, 6.184 mmol). This solution was heated to 95 C for 4 hours, then the solvent was removed and the resulting compound was washed three times with CH3CN (50 mL), dichloromethane (50 mL), and CH3CN (50 mL). After evaporation, the compound was redissolved in -20 C n-BuOH to give pure sceptrin 1 (256 mg, 72% yield from 41) as a pale yellow powder.