Organic & Biomolecular Chemistry 2015-03-21

One-step protecting-group-free synthesis of azepinomycin in water.

Adam J Coggins, Derek A Tocher, Matthew W Powner

Index: Org. Biomol. Chem. 13(11) , 3378-81, (2015)

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Abstract

We report an efficient, atom economical general acid-base catalyzed one-step multi-gram synthesis of azepinomycin from commercially available compounds in water. We propose that the described pH-dependent Amadori rearrangement, which couples an amino-imidazole and simple sugar, is of importance as a potential step toward predisposed purine nucleotide synthesis at the origins of life.