2007 Alkaloids U 0600 A Novel Synthesis of the 2-Aminoimidazol-4-carbaldehyde Derivatives, Versatile Synthetic Intermediates for 2-Aminoimidazole Alkaloids. — In contrast to the pre- viously reported reaction of 2-haloketones with acetylguanidine the reaction of (I) with alkoxycarbonyl guanidines unexpectedly yields ring acylated imidazoles (III). Their conversion to aldehydes (VI) is demonstrated thus allowing the total synthesis of the alkaloids oroidin (VIIa), hymenidin (VIIb), dispacamide (VIIIa) and desbromodispac- amide (VIIIb). — (ANDO*, N.; TERASHIMA, S.; Synlett 2006, 17, 2836-2840; Discovery Res. Lab., Kyorin Pharm. Co., Ltd., Shimotsuga, Tochigi 329-01, Japan; Eng.) — Mais 10- 212

A Novel Synthesis of the 2-Aminoimidazol-4-carbaldehyde Derivatives, Versatile Synthetic Intermediates for 2-Aminoimidazole Alkaloids

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Page 1: A Novel Synthesis of the 2-Aminoimidazol-4-carbaldehyde Derivatives, Versatile Synthetic Intermediates for 2-Aminoimidazole Alkaloids

2007

AlkaloidsU 0600 A Novel Synthesis of the 2-Aminoimidazol-4-carbaldehyde Derivatives, Versatile

Synthetic Intermediates for 2-Aminoimidazole Alkaloids. — In contrast to the pre-viously reported reaction of 2-haloketones with acetylguanidine the reaction of (I) with alkoxycarbonyl guanidines unexpectedly yields ring acylated imidazoles (III). Their conversion to aldehydes (VI) is demonstrated thus allowing the total synthesis of the alkaloids oroidin (VIIa), hymenidin (VIIb), dispacamide (VIIIa) and desbromodispac-amide (VIIIb). — (ANDO*, N.; TERASHIMA, S.; Synlett 2006, 17, 2836-2840; Discovery Res. Lab., Kyorin Pharm. Co., Ltd., Shimotsuga, Tochigi 329-01, Japan; Eng.) — Mais

10- 212